The Best Stationary Lover Gifts (2026 Edition)

**Please note that this The Best Stationary Lover Gifts (2026 Edition) gift guide will be updated and recirculated periodically to reflect the most up-to-date information. This gift guide was most recently updated as of October 2026.***

With personalized options to gorgeous sets, these are the best Stationary Lover Gifts of the season to treat your loved ones!

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. 

Get the Latest Preppy Deals

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

The Best Stationary Lover Gifts (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands, including where to buy Lilly Pulitzer Dupes Besides Amazon, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides.

And if you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including gifts with a preppy vibe, then check out my ChappyWrap review, preppy Fall dresses from Amazon shopping guide, the best preppy places to shop, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

For more up-to-date gift guides, be sure to check out where to buy the best gifts for cocktail lovers, best hostess gifts under $30, best Preppy Gift Ideas, best beach lovers gifts, best travel gifts, best History Lover gifts, best Flower Lovers Gifts, preppy monogrammed gifts, personalized gifts for chefs from a home chef, best champagne lover gifts, best dog lover gifts, best ice cream lovers gifts, best coffee gifts for coffee lovers, best gifts for the art lovers, best gifts for the Margarita lovers, best books about First Ladies guide, best gifts for National Park Lovers gift guide, best London-themed gifts gift guide, best gifts for nature lovers gift guide, best gifts for the gardener gift guide, Washington, DC-Themed Gifts Guide, best Presidential history books from an American History enthusiast guide, best Washington, DC experience gifts guide, bird gifts for bird lovers gift guide and gifts for Martini lovers gift guide.

Planning a trip abroad?! It is always cellular service and data should be the least of your worries! Activate your very own Holafly eSIM to enjoy the peace of mind and perks of unlimited data like back at home with no roaming charges or hassles of physical SIM cards. Use discount code “KATTHO” to receive an exclusive discount upon purchasing your Holafly eSIM today!  

The Best Stationary Lover Gifts (2026 Edition)

After putting together this Stationary Lover Gifts guide, I feel SOOOO tempted to get myself a set of monogrammed stationary for myself as the options are SOOOO good!! The Best part?! Gifts are all primarily under $100 and starting at around $10!

 

Wrap-Up

Cheers to sending more snail mail and treating the stationary lovers in your life!

XOXO – Katie <3 

The Best Preppy Gift Ideas From A Fellow Preppy (2026 Edition)

***Please note that this The Best Preppy Gift Ideas From A Fellow Preppy (2026 Edition) gift guide will be updated and recirculated periodically to reflect the most up-to-date information. This gift guide was most recently updated as of October 2026.***

As a proud preppy fashion enthusiast, I have proudly curated some of the best preppy gift ideas for you to peruse and treat your loved ones to!

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. 

Get the Latest Preppy Deals

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

The Best Preppy Gift Ideas From A Fellow Preppy (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling preppy gift ideas, including where to buy Lilly Pulitzer Dupes Besides Amazon, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides.

And if you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including gifts with a preppy vibe, then check out my ChappyWrap review, preppy Fall dresses from Amazon shopping guide, the best preppy places to shop, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

For more up-to-date gift guides, be sure to check out where to buy the best gifts for cocktail lovers, best hostess gifts under $30, best stationary lovers gifts, best beach lovers gifts, best travel gifts, best History Lover gifts, best Flower Lovers Gifts, preppy monogrammed gifts, personalized gifts for chefs from a home chef, best champagne lover gifts, best dog lover gifts, best ice cream lovers gifts, best coffee gifts for coffee lovers, best gifts for the art lovers, best gifts for the Margarita lovers, best books about First Ladies guide, best gifts for National Park Lovers gift guide, best London-themed gifts gift guide, best gifts for nature lovers gift guide, best gifts for the gardener gift guide, Washington, DC-Themed Gifts Guide, best Presidential history books from an American History enthusiast guide, best Washington, DC experience gifts guide, bird gifts for bird lovers gift guide and gifts for Martini lovers gift guide.

Planning a trip abroad?! It is always cellular service and data should be the least of your worries! Activate your very own Holafly eSIM to enjoy the peace of mind and perks of unlimited data like back at home with no roaming charges or hassles of physical SIM cards. Use discount code “KATTHO” to receive an exclusive discount upon purchasing your Holafly eSIM today!  

The Best Preppy Gift Ideas From A Fellow Preppy (2026 Edition)

Many of these gifts within my Best Preppy Gift Ideas come from things I have used and continue to use regularly including some items that I’ve been gifted! Items within this gift guide range from $20-$250, but typically don’t exceed $300 unless you decide to add tons of customized items to your cart. Whatever you choose to grab for the Preppy Fashion Enthusiast in your life, you are sure to leave a lasting impression and give them something they’ll cherish and use for years to come!

 

Wrap-Up

Here’s to treating the fellow Preppy Fashion Enthusiasts in YOUR life!!

XOXO – Katie <3

Is ChappyWrap Worth It?! Here’s My Consensus!

***Please note that this Is ChappyWrap Worth It?! Here’s My Consensus! product review will be updated and recirculated periodically to reflect the most up-to-date information. This ChappyWrap review was most recently updated as of September 2026.***

While amazingly soft, durable, and cozy ChappyWrap blankets do come at quite a hefty price tag. I’ve personally owned a ChappyWrap since 2023 and hope to shed some light as to whether or not I think the popular blanket is worth the hype.

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. 

Get the Latest Preppy Deals

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling pajamas like LAKE Pajamas, including where to buy Lilly Pulitzer Dupes Besides Amazon, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides.

And if you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including brands like LAKE Pajamas, then check out my preppy Fall dresses from Amazon shopping guide, the best preppy places to shop, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

For more up-to-date gift guides, be sure to check out where to buy the best champagne lover gifts, best dog lover gifts, best ice cream lovers gifts, best coffee gifts for coffee lovers, best gifts for the art lovers, best gifts for the Margarita lovers, best books about First Ladies guide, best gifts for National Park Lovers gift guide, best London-themed gifts gift guide, best gifts for nature lovers gift guide, best gifts for the gardener gift guide, Washington, DC-Themed Gifts Guide, best Presidential history books from an American History enthusiast guide, best Washington, DC experience gifts guide, bird gifts for bird lovers gift guide and gifts for Martini lovers gift guide.

Planning a trip abroad?! It is always cellular service and data should be the least of your worries! Activate your very own Holafly eSIM to enjoy the peace of mind and perks of unlimited data like back at home with no roaming charges or hassles of physical SIM cards. Use discount code “KATTHO” to receive an exclusive discount upon purchasing your Holafly eSIM today!  

Is ChappyWrap Worth It?! Here’s My Consensus!

Table of Contents

About ChappyWrap

Key Features

ChappyWrap Blanket Sizing

My Experience

Is ChappyWrap Worth It?!

My Picks!

About ChappyWrap

It all started with a beloved blanket gifted to its founder Beth in 1965 that her family fought over for generations. It also became a running family joke that Beth should start a business. In 2006, Beth did just that with an MBA and entrepreneurial spirit in hand and a mission to create a soft, durable, and shareable blanket, and hence, ChappyWrap was born!

Initially, Beth sold ChappyWraps at local Boston markets and school fundraisers that soon turned into families lining up to bring their families together, one blanket at a time. As ChappyWrap rapidly grew in popularity, so did the family business when in 2018 Beth’s daughter Christina joined ChappyWrap. 

ChappyWrap is more than just blankets – it’s proudly about family, love, and comfort. Though Beth passed away in March 2025, ChappyWrap is proudly still a family-run business that honors her legacy and heart. Today, Beth’s daughter Christina carries ChappyWrap forward, honoring Beth’s legacy and continuing to led with its core family-led values.

Key Features

Blankets come in several colors, prints, and sizes. ChappyWrap’s blankets have a couple of notable key features, including:

  • Unmatched Quality – All blankets are made with a unique blend that is pill-resistant, irresistibly soft, and breathable.
  • Ideal Weight – These blankets are warm enough to leave you cozy, but light enough to last you throughout the year.
  • Machine Washable – ChappyWrap blankets are made to hold up to everyday’s life moments, while also delivering long-lasting softness.
  • Perfectly Giftable – ChappyWraps can be personalized, making it the perfect gift for anyone for any occasion!

Check out more information on ChappyWrap’s key features here.

ChappyWrap Blanket Sizing

One of the most unique features about ChappyWraps is that they come in 6 different sizes and varieties – perfectly suited for everyone and every occasion. These sizes include:

  • Mini (30″ x 40″) – Made for babies and small pets
  • Midi (40″ x 60″) – Made for kids, travel, or at your desk
  • Original (60″ x 80″) – Made for year-round, everyday comfort 
  • Daytripper (60″ x 80″) – Made for outdoor lounging, anywhere, anyday
  • Lightweight (60″ x 80″) – Made for warmer days and travel
  • Family-size (90″ x 90″) – Made for extra large comfort including King and Queen beds

Check out more information on ChappyWrap blanket sizing here.

My Experience

I cannot not share about my own experience with a ChappyWrap in this ChappyWrap review! I’ve had my *very own* ChappyWrap since 2023 as a Christmas gift to me (from me!). Both me and my dog LOVE my ChappyWrap blanket for snuggling on my Queen-sized bed, especially during the cooler months. 

One of the key aspects of my ChappyWrap that I LOVE is that it is reversible (as all of them are!) and showcases a unique color combination of the same print on each side – something that I LOVE showcasing to make my bed more fun when I change the sheets. At the same time, my ChappyWrap doesn’t get too messy even though it can occasionally be covered in dog hair!

Every Fall season, I look forward to putting my ChappyWrap on my bed to kick off the cozy season and cooler days ahead! As a mega Fall and Winter enthusiast, ChappyWrap makes the season SO MUCH MORE cozy for both me and my dog Rosie (whose ALSO a huge fan!!). 

Is ChappyWrap Worth It?!

This ChappyWrap review answers the question you came here for: IS ChappyWrap worth it?! 

YES! 

While ChappyWraps do come at a hefty price, they are 1000% worth the price and hype. Not only will you LOVE your blanket wherever you decide to use it, but so will those in your life whether it be family, friends, a partner, or pets. ChappyWraps are 10000% worth it for both you and your loved ones to cherish more cozy memories together.

My Picks!

As a fellow ChappyWrap enthusiast, I cannot wrap up this ChappyWrap review without sharing some of my favorite blankets!

 

Wrap-Up

As a big fan myself, this ChappyWrap review sheds some light on this incredible family-owned brand that’s on a mission to celebrate family, love, and comfort and is doing just that. Here’s to making more cozy memories with family, love, comfort, and a ChappyWrap by our sides!

XOXO – Katie <3

Where To Buy The Best Red Wine Lover Gifts From A Fellow Enthusiast (2026 Edition)

***Please note that this Where To Buy The Best Red Wine Lover Gifts From A Fellow Enthusiast (2026 Edition) gift guide will be updated and recirculated periodically to reflect the most up-to-date information. This gift guide was most recently updated as of September 2026.***

Calling all red wine lovers!!! As a proud red wine lover, I have curated a list of where to buy the best red wine lovers gifts as well as a few picks of my own for the red wine lovers in your life. 

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. 

Get the Latest Preppy Deals

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

Where To Buy The Best Red Wine Lover Gifts From A Fellow Enthusiast (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling red wine lover gifts, including where to buy Lilly Pulitzer Dupes Besides Amazon, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides.

And if you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including brands like LAKE Pajamas, then check out my ChappyWrap review, preppy Fall dresses from Amazon shopping guide, the best preppy places to shop, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

For more up-to-date gift guides, be sure to check out where to buy the best gifts for cocktail lovers, best hostess gifts under $30, best stationary lovers gifts, best preppy gift ideas, best Beach Lover gifts, best travel gifts, best History Lover gifts, best Flower Lovers Gifts, preppy monogrammed gifts, personalized gifts for chefs from a home chef, best champagne lover gifts, best dog lover gifts, best ice cream lovers gifts, best coffee gifts for coffee lovers, best gifts for the art lovers, best gifts for the Margarita lovers, best books about First Ladies guide, best gifts for National Park Lovers gift guide, best London-themed gifts gift guide, best gifts for nature lovers gift guide, best gifts for the gardener gift guide, Washington, DC-Themed Gifts Guide, best Presidential history books from an American History enthusiast guide, best Washington, DC experience gifts guide, bird gifts for bird lovers gift guide and gifts for Martini lovers gift guide.

Planning a trip abroad?! It is always cellular service and data should be the least of your worries! Activate your very own Holafly eSIM to enjoy the peace of mind and perks of unlimited data like back at home with no roaming charges or hassles of physical SIM cards. Use discount code “KATTHO” to receive an exclusive discount upon purchasing your Holafly eSIM today!  

Where To Buy The Best Red Wine Lover Gifts From A Fellow Enthusiast 

Amazon 

Amazon has PLENTY of options when it comes to red wine lover gifts some of which *even* has customization options! Shop red wine lover gifts at Amazon here.

Etsy

Etsy is the perfect place to support small businesses and independent artisans and sellers, especially for unique and made with love personalized gifts for chefs! Shop red wine lover gifts on Etsy here.

Mark & Graham

Created in a San Francisco studio, Mark & Graham provides personalized colorful gifts, ranging from glassware, linens, bags, jewelry, travel accessories, and more. You can also shop Mark & Graham here.

Target

Target has several gifts for the red wine lovers in YOUR life from coffee table books to wine glasses to a variety of red wine bottles! Operating over 2,000 stores across the United States, Target is a premier general merchandise retailer selling everything from groceries to clothing for the entire family to home items to electronics and everything in between. Shop at Target here.

My Picks!

 

Wrap-Up

Let’s Raise a glass to treating the red wine lovers in YOUR life!

XOXO – Katie <3

Where To Buy The Best Preppy Monogrammed Gifts (2026 Edition)

***Please note that this Where To Buy The Best Preppy Monogrammed Gifts (2026 Edition) gift guide will be updated and recirculated periodically to reflect the most up-to-date information. This gift guide was most recently updated as of September 2026.***

I am a proud preppy fashion enthusiast! And, I know you’re here to find where to buy the best preppy monogrammed gifts for the preppy fashion enthusiast in your life. From bags to pouch to towels to even vases and everything in between, I have found the best places to buy preppy monogrammed gifts from my own personal experiences.

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. 

Get the Latest Preppy Deals

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

Where To Buy The Best Preppy Monogrammed Gifts (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling preppy monogrammed gifts, including ChappyWrap review, where to buy Lilly Pulitzer Dupes Besides Amazon, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides.

And if you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including brands like LAKE Pajamas, then check out my preppy Fall dresses from Amazon shopping guide, the best preppy places to shop, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

For more up-to-date gift guides, be sure to check out where to buy the best gifts for cocktail lovers, best hostess gifts under $30, best stationary lovers gifts, best preppy gift ideas, best Beach Lover gifts, best travel gifts, best History Lover gifts, best Flower Lovers Gifts, best champagne lover gifts, best dog lover gifts, best ice cream lovers gifts, best coffee gifts for coffee lovers, best gifts for the art lovers, best gifts for the Margarita lovers, best books about First Ladies guide, best gifts for National Park Lovers gift guide, best London-themed gifts gift guide, best gifts for nature lovers gift guide, best gifts for the gardener gift guide, Washington, DC-Themed Gifts Guide, best Presidential history books from an American History enthusiast guide, best Washington, DC experience gifts guide, bird gifts for bird lovers gift guide and gifts for Martini lovers gift guide.

Planning a trip abroad?! It is always cellular service and data should be the least of your worries! Activate your very own Holafly eSIM to enjoy the peace of mind and perks of unlimited data like back at home with no roaming charges or hassles of physical SIM cards. Use discount code “KATTHO” to receive an exclusive discount upon purchasing your Holafly eSIM today!  

Where To Buy The Best Preppy Monogrammed Gifts 

Amazon 

Believe it or not, Amazon has PLENTY of options when it comes to preppy monogrammed gifts! There are several Amazon sellers that specialize in personalized goods as well as Monogramming. Shop preppy monogrammed gifts on Amazon here.

BaubleBar

Accessories designed to tell your story, BaubleBar designs customizable jewelry, bags, and everything in between for YOU to tell your story and design something that’s uniquely yours. Shop BaubleBar here.

Barrington Gifts

A Texas-based leather goods brand, Barrington Gifts specializes in designed customized (including monogrammed!) luxury leather goods – including handbags, totes, and travel accessories at a much more affordable price point. Shop Barrington Gifts here.

Canvas Style

A Texas-based leather goods brand, Barrington Gifts specializes in designed customized (including monogrammed!) luxury leather goods – including handbags, totes, and travel accessories at a much more affordable price point. Shop Barrington Gifts here.

Etsy

Etsy is the perfect place to support small businesses and independent artisans and sellers, especially for unique and made with love personalized gifts for chefs! Shop preppy monogrammed gifts on Etsy here.

Jack Rogers

Jack Rogers began in 1960 during an Italian holiday with a desire to find a beautiful leather sandal. It wasn’t until Jackie Kennedy discovered the Jack Rogers sandal that they rose to the popularity that they have to this day as a preppy sandal staple. Shop Jack Rogers here.

Kendra Scott

Founded by jewelry designer Kendra Scott who started her popular Austin, Texas-based brand from the ground up, Kendra Scott has since turned into an ultra well-known jewelry brand known for offering luxurious jewelry at affordable and accessible price points. Shop Kendra Scott here.

Lands’ End

Lands’ End has been proudly pioneering the way for beautiful, classic, and versatile clothing and footwear for the whole family since 1963 with size inclusion in mind. Shop Lands’ End here. 

Little Words Project

With a mission to inspire and encourage people to be kind to themselves and pay that kindness forward to others, one bracelet at a time, Little Words Project is a popular bracelet brand that truly lives up to its mission and vision. Shop Little Words Project here.

LL Bean

With a core belief that the more time we spend outside together, the better, LL Bean’s roots began in Maine when Leon Leonwood Bean invented the Maine Hunting Shoe in 1911. Over a century later, LL Bean is still going strong, selling the popular LL Bean bean boots, personalized canvas totes, and preppy outerwear apparel, all with its Maine roots at the heart of everything. Shop LL Bean here. 

Mark & Graham

Created in a San Francisco studio, Mark & Graham provides personalized colorful gifts, ranging from glassware, linens, bags, jewelry, travel accessories, and more. You can also shop Mark & Graham here.

Navy Bleu

With designs originating in Massachusetts, Navy Bleu is a resort wear brand offering exclusive, small-batch apparel and home decor. Shop Navy Bleu here.

Scout Bags

Named after founder Deb Waterman Johns dachshund Scout, Scout Bags is a Washington, DC-based bag brand that designs bags in life proof fabric (can personally confirm and swear by them!!!). They fit for everything you need throughout daily life, whether it be grocery shopping, organization, travel, carpool, potlucks, and more. Shop Scout Bags here.

Sprinkled with Pink

With an all-female, woman-owned team based out of Dallas, Texas, Sprinkled with Pink brings the magic into every moment with personalized gifts, bags, clothing, and accessories for every occasion at an accessible price point. Shop Sprinkled with Pink here.

Stoney Clover Lane

Offering customizable leather and nylon accessories and bags with their ultra-fun array of patches to choose from, Stoney Clover Lane is a one-stop shop to make any accessory super bubbly and uniquely yours. Shop Stoney Clover Lane here.

The Monogram Corner

Infused with Northeastern Preppy Style, The Monogram Corner is a small business that specializes in a collection of curated personalized clothing, jewelry, home decor, and accessories. Shop The Monogram Corner here.

United Monograms

A well-known online shop for all-things monograms, United Monograms offers monogrammed and personalized goods with both trendy and classic flairs. Shop United Monograms here.

Vera Bradley

Started in 1982 in Fort Wayne, Indiana by friends Barbara Bradley Baekgaard and Patricia R. Miller, Vera Bradley has since become a popular luggage and handbag brand known for its iconic quilted cotton designs in colorful and fun patterns, including collaborations with colleges and the NFL. Shop Vera Bradley here.

Weezie

Weezie is a luxury monogrammed towels and clothing brand where its materials are all OEKO-TEX® certified and low-linting. Shop Weezie here.

My Picks!

 

Wrap-Up

Cheers to spoiling the preppy fashion enthusiasts in YOUR life! 

XOXO – Katie <3

Where To Buy Pajamas Like LAKE Pajamas That Are Soft + Stylish

***Please note that this Where To Buy Pajamas Like LAKE Pajamas That Are Soft + Stylish shopping guide will be updated and recirculated periodically to reflect the most up-to-date information. This shopping guide was most recently updated as of September 2026.***

If you’re like me and you love the look of LAKE Pajamas yet are a bit intimidated by the cost (I was, too, at first!), then you need to keep these pajama brands on your radar!

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling pajamas like LAKE Pajamas, including ChappyWrap review, where to buy Lilly Pulitzer Dupes Besides Amazon, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides.

And if you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including brands like LAKE Pajamas, then check out my preppy Fall dresses from Amazon shopping guide, the best preppy places to shop, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

Get the Latest Preppy Deals

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page.

Where To Buy Pajamas Like LAKE Pajamas That Are Soft + Stylish

When shopping for the perfect pajamas, including finding pajama brands like LAKE Pajamas, it can be a bit daunting! In this guide, I’ve rounded up my top 5 favorite pajama brands after trying 20+ brands’ pajamas.

Where To Buy Pajamas Like LAKE Pajamas

Buy Pajamas Like LAKE Pajamas on Amazon

Amazon has a variety of budget-friendly pajamas like LAKE Pajamas that will do the trick. However, it is important to note that Amazon’s inventory is ever-evolving and changes daily. Shop the latest and greatest LAKE Pajamas lookalikes on Amazon here.

Crown & Ivy at Belk

Started in 2014, Crown & Ivy is a Belk-exclusive brand selling all-things colorful and preppy. You can also shop Crown & Ivy here. 

Joyspun at Walmart: Buy Affordable Pajamas Like LAKE

Joyspun is a Walmart-exclusive pajama and intimates brand (and more!). Plus, it sells items in sizes XS-3XL, making it an affordable and size-inclusive brand. Better yet, Joyspun carries maternity intimates, slippers, robes, socks, and shapewear (none of which I have yet to purchase and try out for myself). Shop Joyspun here. 

Katie Kime: Buy Printed Pajamas Like LAKE

Founded by Austin, Texas-based fashion designer Katie Kime who is a Duke University graduate and North Carolinian, Katie Kime designs are made-to-order and inspired by the American South and Kime’s travels with a colorful, modern, and traditional flair. Shop Katie Kime here.

Kim Rogers at Belk

Kim Rogers is an affordable Belk-exclusive brand that offers bright colors and highly detailed designs. You can also shop Kim Rogers here. 

Lands’ End

Lands’ End has been proudly pioneering the way for beautiful, classic, and versatile clothing and footwear for the whole family since 1963 with size inclusion in mind. You can also shop Lands’ End here. 

Laura Ashley: Buy Floral Pajamas Like LAKE

Founded by Welsh fashion designer Laura Ashley who originally made furnishing materials in the 1950s and expanded into clothing in the 1960s, Laura Ashley has since become a popular fashion and interior design brand that is still in business today, even after Ashley’s passing in 1985. Shop Laura Ashley at TJ Maxx here and Marshall’s here.

LOFT

Founded in 1998, LOFT is a well-known women’s wear fashion brand and sister brand to Ann Taylor that empowers women to feel their best on a budget whether in the workplace, at home, a night out, or on vacation. You can also shop LOFT here. 

Mark & Graham

Created in a San Francisco studio, Mark & Graham provides personalized colorful gifts, ranging from glassware, linens, bags, jewelry, travel accessories, and more. You can also shop Mark & Graham here.

Mary Square: Buy Bright Pajamas Like LAKE

A women-owned brand founded by Kelly Shiley. Mary Square designs bright printed clothing to inspire joy, brighten one’s day, and build confidence. Read my Mary Square pajamas review here and get 15% Off Your Entire Order at Mary Square with code THEPINKCHICKADEE.

Quince

Quince focuses on bringing high-end, luxury materials such as cashmere, Mongolian wool, and linen at an affordable price point all with sustainability and using recycled materials in mind. You can also shop Quince here. 

The Royal Standard

Providing a curated selection of home goods, accessories, holiday decor, gifts, clothing, and their ultra-soft pajamas, The Royal Standard offers it all with a traditional Southern flair at accessible price points. Shop The Royal Standard on Amazon here.

Tuckernuck

Taking its namesake from Summers on Nantucket via the nearby island Tuckernuck, Tuckernuck focuses on designing gorgeous preppy fashion with price ranges and styles from affordable luxury to high-end investment pieces. Shop Tuckernuck here.

Wrap-Up

Until next time, happy pajama shopping, fellow LAKE Pajamas fans!

XOXO – Katie <3 

The Best Preppy Places To Shop As A Forever Preppy (2026 Edition)

***Please note that this The Best Preppy Places To Shop As A Forever Preppy guide will be updated and recirculated periodically to reflect the most up-to-date information. This shopping guide was most recently updated as of August 2026.***

As a forever preppy fashion lover, I have found several preppy places to shop and, in this shopping guide, I am spilling ALLL the tea on the best preppy places to shop at!!

If you also love preppy fashion brands, including ChappyWrap review, boutiques like Avara, brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck and where to buy dresses like Tuckernuck guides. If you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

For *even* more preppy style inspiration including brands like Lilly Pulitzer, then check out my where to buy grandmillennial style clothing guide, preppy Fall dresses from Amazon shopping guide, Lilly Pulitzer Signature Stores master list, preppy clothing brands list, preppy clothes style guide, and styling preppy outfits guide.

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page.

The Best Preppy Places To Shop As A Forever Preppy (2026 Edition)

Online Boutiques & Stores

3 Sisters

Founded and owned by three sisters Stella, Athina and Stavroulla, 3 Sisters is a family-owned boutique selling stylish, trendy, and chic clothing at an affordable price point. Shop 3 Sisters here.

Addison Bay

Designed for the woman on the go, Addison Bay prides itself on creating active wear to wear beyond the gym and where fashion forward doesn’t mean less function. Shop Addison Bay here.

Aryeh Collection

Known for the UPF 50+ and cooling fabrics, Aryeh Collection is a uniquely designed and curated line of stylish detailed watercolor patterned pieces. Shop Aryeh Collection here.

Avara

Avara focuses on high quality and cute clothing with a colorful, boutique-like flair since its founding by Emily Wickard in 2018. Shop Avara here.

BaubleBar

Accessories designed to tell your story, BaubleBar designs customizable jewelry, bags, and everything in between for YOU to tell your story and design something that’s uniquely yours. Shop BaubleBar here.

Barrington Gifts

A Texas-based leather goods brand, Barrington Gifts specializes in designed customized (including monogrammed!) luxury leather goods – including handbags, totes, and travel accessories at a much more affordable price point. Shop Barrington Gifts here.

Becky’s Boutique 

With 30+ years of retail experience under her belt, Becky was on a mission to open a boutique that brings the best styles to Northern Virginia (and beyond!) with a deeper understanding for what her customers want to feel and look their best. Shop Becky’s Boutique here.

Beyond By Vera

Designed by Austrian designer Vera Fritsch, Beyond By Vera designs garments to elevate everyday style all with original, hand-drawn prints/ Truly, all of Beyond By Vera’s pieces are reimagined as wearable art. Shop Beyond By Vera here.

BloomChic

A digital fashion-first brand, BloomChic prides itself on creating size-inclusive fashion options for mid and plus size women sizes 10-30 at an affordable price point. Shop BloomChic here.

Boden

Dating back to 1991 as a mail-order catalog business in the United Kingdom, Boden has since crossed the pond to the United States where its clothing is loved by both nations with its bright and bubbly prints. Shop Boden here.

Brooks Brothers

Since 1818 Brooks Brothers has been designing timeless American preppy apparel for women, men, and children. Shop Brooks Brothers here.

Cabana Life

Founded by Melissa Marks, a melanoma survivor, Cabana Life’s stylish and preppy pieces will take you from a day on the beach to a happy hour at sunset while keeping you protected from the sun. Sun safety awareness is a big proponent of Cabana Life’s mission and philosophy and the brand has a UPF 50+ rating, to ensure you feel great while looking it, too. Shop Cabana Life here.

Canvas Style

Canvas Style is a lifestyle and jewelry brand that empowers women to celebrate their style through accessible luxury products. Shop Canvas Style here.

Case-Mate

Case-Mate sells all-things adorable waterproof accessories ranging from bags to phone cases to pouches and everything in between. Shop Case-Mate here.

ChappyWrap

ChappyWrap started with a cherished comfortable and cozy family blanket that they couldn’t find anything like years’ later, so its founder Beth sought out to create her own and hence ChappyWrap known for their ultra soft and comfortable blankets was born. Shop ChappyWrap here.

Draper James

Launched in 2015 by “Legally Blonde” actress Reese Witherspoon, Draper James is a fashion brand that pays homage to the actress’s “Southern roots and personal style” and is notably named after her grandparents Dorothea Draper and William James Witherspoon. Shop Draper James on their website here and bedding + pajamas at Kohl’s here.

Dudley Stephens

A woman-owned business created for the woman who values versatility in her wardrobe as opposed to following the latest trends, Dudley Stephens designs all of their products with recyclable materials and gives back to helping women and children in need. Shop Dudley Stephens here.

Duffield Lane

Founded by Jamie Duffield who left her career as a lawyer to pursue her passion for fashion in 2013, Duffield was on a mission to find high-quality pajamas that feel as good as they look and, hence, Duffield Lane was born! Shop Duffield Lane here.

Emily McCarthy

Rooted in Emily McCarthy’s fine arts and graphic design background, Emily McCarthy is a Savannah, Georgia-based fashion brand focused on empowering women to feel their expressive and confident in all aspects of their lives. Shop Emily McCarthy here.

Furbish Studio

A Raleigh, North Carolina-based home decor accents studio, Furbish Studio specializes in vibrant home accent pieces, specifically their needlepoint pillows and goods, that leave your home feeling uniquely yours. Shop Furbish Studio here.

Grace Karin

A popular seller on Amazon known for its Bridgerton-inspired dresses and preppy pieces, Grace Karin’s dresses retail at a fraction of the cost compared to Lilly Pulitzer. Shop Grace Karin here.

Gretchen Scott Designs 

Living by the motto “Laugh More, Gripe Less, Ignore Critics, Say Yes, Order Dessert, Love Life,” Gretchen Scott Designs’ founder and CEO Gretchen Scott specializes in super fun, chic, and globally-inspired designs often in a bright and bubbly fashion. Shop Gretchen Scott Designs here.

Happy Place 

Known as the place where everything is Pink-tastic, Happy Place is founded by the owners of 3 Sisters and The Lucky Knot – three sisters Stella, Athina and Stavroulla. Truly, upon walking into Happy Place you feel as if you’ve entered into Barbie’s dream house, with all of the vibrant merchandise – truly it is a pink paradise at Happy Place! Shop Happy Place here.

Hill House Home

Founded in 2016 by London native and New York living Nell Diamond, Hill House Home brings romantic and dreamy styles through Diamond’s dream to make “happy things for happy places.” Hill House Home’s most well-known garment is their Nap Dress, which I have created both a Nap Dress review for here and a Nap Dress dupe shopping guide for here. Shop Hill House Home here.

Ivy City Co.

Founded by 3 women navigating the early stages of motherhood, Ivy City Co. sells modest size-inclusive dresses that inspire women to embrace their femininity and celebrate togetherness and community. Shop Ivy City Co. here.

Jack Rogers

Jack Rogers began in 1960 during an Italian holiday with a desire to find a beautiful leather sandal. It wasn’t until Jackie Kennedy discovered the Jack Rogers sandal that they rose to the popularity that they have to this day as a preppy sandal staple. Shop Jack Rogers here.

J Crew/J Crew Factory

Founded in 1983, J Crew is a renowned American preppy fashion brand known for its classic and affordable styles with an emphasis on high quality. J Crew also brings its preppy and classic A-game at an even affordable price range via its outlet store J Crew Factory. Shop J Crew here and shop J Crew Factory here.

J. McLaughlin

Started by two brothers Kevin and Jay McLaughlin in 1977, J. McLaughlin has since become a visionary of timeless style with stores all across the United States. Shop J. McLaughlin here.

Johnnie-O

Dating back to 2005 and founded by NCAA and Senior’s Open-championship golfer John O’Donnell, Johnnie-O had a vision to create a simple, high-quality golf shirt. Since 2005, Johnnie-O has expanded into selling women’s wear and children’s golf apparel. Shop Johnnie-O here.

Joules

Joules is a British fashion and home goods brand founded by Tom Joule and inspired by the British countryside. Shop Joules on Amazon here.

Jude Connally

Founded in 2010 by a busy working mother Jude Connally Zimmerman, Jude Connally is an American-made women’s fashion brand that focuses on empowering women to look great, feel great, and have easy to care for pieces that mold into their busy lives. Shop Jude Connally here.

Kate Spade New York

An American Fashion house founded in January 1993 by Kate and Andy Spade with a mission to create affordable luxury designer fashion products in Manhattan, Kate Spade New York is a popular fashion brand known for its unique novelty bags and vibrant high fashion garments. Shop Kate Spade New York here and the Kate Spade Outlet here.

Katie Kime

Founded by Austin, Texas-based fashion designer Katie Kime whose a Duke University graduate and North Carolinian, Katie Kime designs are made-to-order and inspired by the American South and Kime’s travels with a colorful, modern, and traditional flair. Shop Katie Kime here.

Kendra Scott

Founded by jewelry designer Kendra Scott who started her popular Austin, Texas-based brand from the ground up, Kendra Scott has since turned into an ultra well-known jewelry brand known for offering luxurious jewelry at affordable and accessible price points. Shop Kendra Scott here.

LAKE

Founded by Anne Read Lattimore and Cassandra Cannon in Savannah, Georgia in 2014, LAKE is a luxury sleepwear pajama brand known for some of the softest high-quality cotton pajamas ever worn that are worth the $100+ price tag (can personally confirm!!!), alongside soft lounge apparel. Shop LAKE here.

Lands’ End

Lands’ End has been proudly pioneering the way for beautiful, classic, and versatile clothing and footwear for the whole family since 1963 with size inclusion in mind. Shop Lands’ End here.

Lele Sadoughi

A Dallas, Texas-based well-known accessories brand founded by Lele Sadoughi, Lele Sadoughi designs maximalist accessories, ranging from headbands, jewelry, and other accessories with fun collaborations including with the NFL and MLB. Shop Lele Sadoughi here.

Lilly Pulitzer

Starting with a juice stand in the 1960s when Lilly Pulitzer was looking to design a garment with bright and bubbly prints to cover up juice stains in Palm Beach, Florida, Lilly Pulitzer has since been a popular luxury resort wear and lifestyle brand known for their Palm Beach-inspired prints. Shop Lilly Pulitzer here.

Lisi Lerch

After many years working on Wall Street, Lisi Lerch started her statement accessories brand in the spring of 2001 with vintage-inspired statement jewelry, handbags, and accessories fit to make every look sparkle. Shop Lisi Lerch here.

Little Words Project

With a mission to inspire and encourage people to be kind to themselves and pay that kindness forward to others, one bracelet at a time, Little Words Project is a popular bracelet brand that truly lives up to its mission and vision. Shop Little Words Project here.

LL Bean

With a core belief that the more time we spend outside together, the better, LL Bean’s roots began in Maine when Leon Leonwood Bean invented the Maine Hunting Shoe in 1911. Over a century later, LL Bean is still going strong, selling the popular LL Bean bean boots, personalized canvas totes, and preppy outerwear apparel, all with its Maine roots at the heart of everything. Shop LL Bean here.

Loeffler Randall

A Brooklyn-based women’s accessories and footwear brand founded by Jessie Randall and her husband Brian Murphy in 2004 started in their apartment, Loeffler Randall has since grown into a well-known brand known for their feminine, chic, and high-quality products all with practicality in mind. Shop Loeffler Randall here.

LOFT

Founded in 1998, LOFT is a well-known women’s wear fashion brand and sister brand to Ann Taylor that empowers women to feel their best on a budget whether in the workplace, at home, a night out, or on vacation. Shop LOFT here.

Longchamp

A French luxury handbags brand known for their iconic Le Pilage bag styled by the likes of Kate Middleton, Meghan Markle, Jennifer Lopez, and Rihanna, Longchamp’s bags are still handcrafted in France with luxury in mind. Shop Longchamp here.

Lou Lou Boutiques

From its roots as a brick and mortar store in 2004 in Middleburg, Virginia with locations across the Mid-Atlantic and South and founded and family owned by Tara and Ben Wegdam, Lou Lou Boutiques has since expanded its footprint to Old Town Alexandria selling a curated collection of women’s wear, accessories, and small gifts. Shop Lou Lou Boutiques here.

LoveShackFancy

LoveShackFancy is the ultimate romantic, floral, and vintage-inspired fashion and lifestyle brand founded in 2013 by Rebecca Hessel Cohen. Shop LoveShackFancy here.

Madison Mathews

Designed with intention in Charleston, South Carolina, Madison Mathews crafts all pieces with 100% cotton and linen in colorful block prints and classic styles. Shop Madison Mathews here.

Maggy London

Dating back to 1979 as a ladies’ silk dress resource, Maggy London is an online retailer that specializes in classic, well-tailored women’s dresses. Shop Maggy London here.

Mahi Gold

Family owned and operated out of Chatham, Massachusetts in the heart of Cape Cod, Mahi Gold is a womenswear brand designing pieces inspired by all-things classic, Americana, and coastal living. Shop Mahi Gold here.

Mackenzie-Childs

A popular hand-painted ceramics and home decor retailer based out of Aurora, New York, Mackenzie-Childs turns everyday things into stylish moments. Shop Mackenzie-Childs here.

Mark & Graham

Created in a San Francisco studio, Mark & Graham provides personalized colorful gifts, ranging from glassware, linens, bags, jewelry, travel accessories, and more. Shop Mark & Graham here.

Mary Square

A women-owned brand founded by Kelly Shiley, Mary Square designs bright printed clothing to inspire joy, brighten one’s day, and build confidence. Read my Mary Square pajamas review here and get 15% Off Your Entire Order at Mary Square with code THEPINKCHICKADEE.

Mint Julep Boutique

Mint Julep Boutique launched in 2012 and has since become an online go-to boutique spot for all of your wardrobe needs. Shop Mint Julep Boutique here.

Navy Bleu

With designs originating in Massachusetts, Navy Bleu is a resort wear brand offering exclusive, small-batch apparel and home decor. Shop Navy Bleu here.

Old Navy

Owned by GAP, Inc., the well-known and budget-friendly American retailer offers all-things casual and fashionable apparel, including preppy pieces at a fraction of the cost. Shop Old Navy here.

Petal & Pup

Petal & Pup’s origins begin in Queensland, Australia as a fashion brand bringing a laid-back and optimistic vibe to all of its designs at an affordable price point. Today, Petal & Pup is a popular retailer selling its designs at Nordstrom and on their website. Shop Petal & Pup on their website here and at Nordstrom here.

Pink City Prints

Designed in London and handcrafted in Jaipur, Pink City Prints designs timeless and elegant block printed clothing and accessories. Shop Pink City Prints here.

Prettygarden

Prettygarden is an Amazon seller well-known for its pretty garden-like apparel. The best part?!? Prettygarden’s dresses like Lilly Pulitzer’s are at a much affordable price point, too! Shop Prettygarden here.

Printfresh

Founded by couple Amy and Leo Voloshin, Printfresh is a popular lifestyle brand well-known for their luxury pajamas that also sells beautiful bright and bubbly dresses, too! Shop Printfresh here.

Queen of Sparkles

With a commitment to make every woman feel as if she can shine a bit brighter, Queen of Sparkles provides unique sequined apparel for just about every occasion. Shop Queen of Sparkles here.

Quince

Quince focuses on bringing high-end, luxury materials such as cashmere, Mongolian wool, and linen at an affordable price point all with sustainability and using recycled materials in mind. Shop Quince here.

Ralph Lauren

Dating back to 1967 with its founding by Ralph Lauren in New York City as a timeless, preppy fashion brand selling menswear, womenswear, home, accessories, and fragrance products, Ralph Lauren has since become a well-known namesake in the fashion industry globally. Shop Ralph Lauren here.

Red Dress

A childhood dream turned into a reality, Red Dress boutique originated over 25 years ago in Athens, Georgia and has since transformed into a well-known boutique with a strong online presence. Shop Red Dress here.

Rifle Paper Co.

Handpainted by Anna Bond, Rifle Paper Co. is a lifestyle brand that beautifully brightens the everyday through stationary, accessories, home goods, and more. Shop Rifle Paper Co. here.

RIHOAS

Inspired by the romance, beauty, artistry, and visual appeal of European cinema, Hong Kong-founded fashion brand RIHOAS brings their inspiration to life through their women’s wear clothing that has a vintage appeal with a sustainable vision for the future. For more information, check out my review of RIHOAS here. Shop RIHOAS here.

Roller Rabbit

A feel-good lifestyle brand selling sophisticated loungewear, accessories, and home goods including their iconic monkey printed pajamas and goods. Roller Rabbit is a well-known brand and has even recently done a collaboration with Target. Shop Roller Rabbit here.

Rothy’s

Selling washable shoes and bags made with recycled materials, Rothy’s has since become a popular shoe brand with the most comfortable and stylish shoes. Shop Rothy’s here.

Sail To Sable

A collection of “chic meets preppy” pieces, Sail to Sable is a fashion and lifestyle brand targeting women of all ages, sizes, and stages of life. Shop Sail to Sable here.

Sara Campbell

Made in factories in New York, New Jersey, and Massachusetts, Sara Campbell is a Boston-based fashion brand selling chic, timeless, and playful apparel. Shop Sara Campbell here.

Sea Bags

Handcrafted designs made from recycled sail cloth in Portland, Maine, Sea Bags sustainably makes nautically-inspired totes and accessories. Shop Sea Bags here.

Sezane

Based in Paris, Sezane is selling chic designer Parisian style with accessibility and affordability at the heart of it all. Shop Sezane here.

Scout Bags

Named after founder Deb Waterman Johns dachshund Scout, Scout Bags is a Washington, DC-based bag brand that designs bags in life proof fabric (can personally confirm and swear by them!!!). They fit for everything you need throughout daily life, whether it be grocery shopping, organization, travel, carpool, potlucks, and more. Shop Scout Bags here.

Sigrid Olsen

Known for her unique prints and “beach to bistro” vibe, Sigrid Olsen attainable and sustainable artisan crafted resort wear. Shop Sigrid Olsen at TJ Maxx here and Marshall’s here.

Simply Southern

Known for their colorful and preppy tees sold at Hallmark and many gift shops throughout the United States. Simply Southern is more than just a t-shirt brand. Simply Southern also sells vibrant and preppy apparel and home decor pieces while supporting nonprofits. Shop Simply Southern here.

Smith & Quinn

Family-run and based in Annapolis, Maryland, Smith & Quinn specializes in high-quality and high-end women’s and men’s sportswear, dresses, and more. Shop Smith & Quinn here.

Spartina 449

Designed in the South Carolina Lowcountry, Spartina 449 prides in bringing the Lowcountry style to everyday life, including with their luxury handbags specifically their destination prints including your favorite destinations, jewelry, coastal clothing, and more. Shop Spartina 449 here.

Southern Tide

Dating back to 2006, Southern Tide was founded in Greenville, South Carolina by Allen Stephenson as a coastal lifestyle apparel brand that honors traditions while charting its own unique course. Shop Southern Tide here.

Sperry

Founded in 1935 by Paul Sperry who was inspired by his dog’s ability to grip ice, Sperry invented the world’s first-ever non-slip boat shoe: the Top Sider. Since then, Sperry has become a popular footwear brand especially for fellow preppy fashion enthusiasts. Shop Sperry here.

Sprinkled with Pink

With an all-female, woman-owned team based out of Dallas, Texas, Sprinkled with Pink brings the magic into every moment with personalized gifts, bags, clothing, and accessories for every occasion at an accessible price point. Shop Sprinkled with Pink here.

Stanley

Originating in 1913 through founder William Stanley Jr.’s revolutionary drink ware innovation via creating vacuum-sealed, all-steel water bottles that replaced glassware, Stanley was initially marketed to outdoors-men including my Papa whose a deer hunter but has since taken off as a preppy water brand via their popular and fire-proof tumblers that have seen it all. Shop Stanley here.

Stella Parker Designs

Stella Parker stylishly makes UPF sun-protective resort wear in vibrant and fun prints. Shop Stella Parker Designs here.

Stoney Clover Lane

Offering customizable leather and nylon accessories and bags with their ultra-fun array of patches to choose from, Stoney Clover Lane is a one-stop shop to make any accessory super bubbly and uniquely yours. Shop Stoney Clover Lane here.

Sugarlips

Sugarlips is a women’s wear brand that sells trendy clothing, including adorable dresses like Lilly Pulitzer’s, all at a deal. Shop Sugarlips here.

Talbots

Dating back to 1947 as a catalog-based brand, Talbots is a preppy, New England lifestyle brand empowering women of all sizes to look and feel their best. Shop Talbots here.

The Beaufort Bonnet Company

Founded by Markey Hutchinson in 2012, The Beaufort Bonnet Company provides timeless and classic upscale clothing and accessories for babies and children, including Mommy and Me styling opportunities. Shop The Beaufort Bonnet Company here.

The Black Dog

With roots out of a captain’s love for the sea, his island home, and most importantly his dog, The Black Dog brand was born with its popular black dog logo on all of its merchandise fit for a day at sea. Shop The Black Dog here.

The Company Store

Providing home goods focused on comfort, versatility, and luxury with a timeless and preppy flair, The Company Store truly has it all in terms of home goods. Shop The Company Store here.

The Impeccable Pig

Originally founded in Dallas, Texas in 2002 by sisters Laura and Mona as a home decor shop, The Impeccable Pig has since evolved into an apparel boutique when Laura’s daughter Jenny joined the team as a buyer in 2005 with multiple boutiques in Texas and an e-Commerce presence and donates to local nonprofits supporting women’s empowerment. Shop The Impeccable Pig here.

The Lucky Knot

As if Vineyard Vines and Lilly Pulitzer had a baby, The Lucky Knot is a preppy and nautical fashion boutique owned by three sisters Stella, Athina and Stavroulla who also own sister shops in Old Town Alexandria – Happy Place and 3 Sisters. The Lucky Knot carries popular preppy fashion brands including Lilly Pulitzer, Sail To Sable, and Gretchen Scott Designs and also has a menswear section. Shop The Lucky Knot here.

The Royal Standard

Providing a curated selection of home goods, accessories, holiday decor, gifts, clothing, and their ultra-soft pajamas, The Royal Standard offers it all with a traditional Southern flair at accessible price points. Shop The Royal Standard on Amazon here.

The Tiny Tassel 

I have been connected to The Tiny Tassel’s store owner the ultra-adorable Mimi for a few years now and have been DYING to check out her stunning storefront for a few years now! I LOVE LOVE LOVE the designs that Mimi designs herself, ranging from beaded earrings and bracelets to clothing. I’ve had a pair of flamingo tassel earrings for over 3 years now! Well, what can I say?! There’s ALWAYS a next time!! Shop The Tiny Tassel here.

Tommy Bahama

Tommy Bahama is a resort wear brand that brings paradise to everyday life (and vacation, too!). Shop Tommy Bahama here.

Tommy Hilfiger

Founded in 1985 by Tommy Hilfiger, Tommy Hilfiger offers classic American-cool, preppy, and nautical apparel for all. Shop Tommy Hilfiger here.

Top It Off Accessories

Based in Boston, Top It Off Accessories sells effortless all-things preppy women’s apparel and accessories designed for real life at an affordable price point. Shop Top It Off Accessories here.

Tory Burch

Blending American style with global influences like travel, color, and architectural details, Tory Burch is a contemporary women’s clothing, shoes, and accessories brand founded and owned by Tory Burch, herself. Shop Tory Burch here.

Trina Turk

Started in 1995 by fashion designer Trina Turk, the Trina Turk collection focuses on creativity, the sunny side, and California’s multicultural melting pot via its optimistic bright and bold designs. Shop Trina Turk here.

Tuckernuck

Taking its namesake from Summers on Nantucket via the nearby island Tuckernuck, Tuckernuck focuses on designing gorgeous preppy fashion with price ranges and styles from affordable luxury to high-end investment pieces. Shop Tuckernuck here.

United Monograms

A well-known online shop for all-things monograms, United Monograms offers monogrammed and personalized goods with both trendy and classic flairs. Shop United Monograms here.

Vera Bradley

Started in 1982 in Fort Wayne, Indiana by friends Barbara Bradley Baekgaard and Patricia R. Miller, Vera Bradley has since become a popular luggage and handbag brand known for its iconic quilted cotton designs in colorful and fun patterns, including collaborations with colleges and the NFL. Shop Vera Bradley here.

Victoria Dunn Design

Designed and inspired in Charleston, South Carolina and manufactured in a fourth generational factory in Jaipur, India, Victoria Dunn Design celebrates generational craftsmanship with its colorful block print apparel. Shop Victoria Dunn Design here.

Vineyard Vines

Founded on Martha’s Vineyard in 1988 by brothers Shep and Ian Murray, Vineyard Vines is an all-things preppy, bright, and Americana fashion brand known for their pink whale logo that makes a splash. Shop Vineyard Vines here.

Weezie

Weezie is a luxury monogrammed towels and clothing brand where its materials are all OEKO-TEX® certified and low-linting. Shop Weezie here.

Wenrine

Wenrine is a popular seller on Amazon known for its preppy dresses like Lilly Pulitzer’s retailing at a fraction of the cost. Shop Wenrine here.

West Indies Wear

West Indies Wear is pure cotton wear made for high heat or tropical getaways that’s extremely fun, vibrant, and colorful. Shop West Indies Wear here.

York Design Co.

Selling needlepoint accessories and bags in the Washington, DC area, York Design Co. is a woman-owned brand made with love that designs and pays it forward with purpose: to support children’s cancer. Shop York Design Co. here.

Department Stores

Belk

A popular Southern department store chained founded in 1888 with its headquarters in Charlotte, North Carolina, Belk‘s influence as a department store with 300+ locations expands beyond the South with its popular e-Commerce platform, too. Alongside selling Lilly Pulitzer pieces (sometimes at a markdown especially in-stores!), Belk also sells well-known brands like Lilly Pulitzer including Mary Square, Vineyard Vines, and their private label brand Crown & Ivy. Shop Belk here.

Dillard’s 

Headquartered in Little Rock, Arkansas, Dillard’s was founded by William T. Dillard in 1938 and is a popular department store in the American South with over 271 stores in 30 states. Besides Lilly Pulitzer, Dillard’s carries popular name brands including Antonio Melani, Abbey Glass, and more! Shop at Dillard’s here.

Marshall’s

Marshall’s, like TJ Maxx, is a popular off-price retailer selling several well-known name brands in the apparel, footwear, accessories, and home departments (fit for everyone in the family). Shop Marshall’s here.

Nordstrom

Dating back to 1901 originally as a shoe store, Nordstrom is a popular Seattle, Washington-based department store chain across the United States with hundreds of stores. Nordstrom sells tons of designer brands such as Longchamp, Tory Burch, and Kate Spade alongside Lilly Pulitzer. Shop at Nordstrom here. 

Nordstrom Rack

Alongside Nordstrom, Nordstrom has its popular outlet sister store Nordstrom Rack (which also sells Lilly Pulitzer, Kate Spade, and Barefoot Dreams!). Shop at Nordstrom Rack here.

TJ Maxx

TJ Maxx is a popular off-price retailer selling several well-known name brands in the apparel, footwear, accessories, and home departments (fit for everyone in the family). Shop TJ Maxx here.

Walmart

Walmart was started in 1962 by Sam Walton in Rogers, Arkansas and has since expanded into one of the world’s leading employers and largest retailers with 10,600+ stores and selling everything from clothing to home to groceries to toys and everything in between – all under one roof (and with a strong e-Commerce front, too!). One of its most popular preppy brands is Free Assembly. Shop at Walmart here.

Wrap-Up

From one proud forever preppy fashion enthusiast to another, happy shopping!!!

XOXO – Katie <3

I’ve Tried Several Preppy Dresses From Amazon: These Are My Picks!

***Please note that this I’ve Tried Several Preppy Dresses From Amazon: These Are My Picks! shopping guide will be updated and recirculated periodically to reflect the most up-to-date information. This shopping guide was most recently updated as of August 2026.***

If you’re a fan of Lilly Pulitzer or Tuckernuck, then you know that there are several preppy dresses from Amazon at a fraction of the cost. This shopping guide will outline preppy dresses: Amazon edition!

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page.

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

I’ve Tried Several Preppy Dresses From Amazon: These Are My Picks!

Looking for ways to save on your favorite preppy brands?!?! Be sure to check out my Poshmark which is updated weekly with the latest & greatest secondhand preppy deals!

 

Know Before You Buy

Before I start sharing some adorable preppy dresses Amazon edition, I am going to share a few things to note before you buy:

  • Prices on many clothing items (like everything else on Amazon) do fluctuate. It is worthwhile to monitor prices on Amazon, enjoy coupons when given the opportunity to.
  • Garments do come and go in and out of stock, like a lot of inventory on Amazon (or anywhere else). Be sure to keep an eye on garments of interest upon buying.
  • Most garments within the Item Description section will have information on material and sizing. I highly recommend looking at that before making a purchase so there are no surprises.
  • Be sure to read product reviews, if you feel nervous before making a purchase. Many product reviews may be bots or spam, so be sure to look for real product images and filter out ratings to get the full scope of what you’re looking to buy before you buy.

Preppy Dresses From Amazon 

For more preppy and grand millennial deals and steals for less, including some excellent preppy places to shop and where to buy grandmillennial style clothing guide, then check out my Amazon Storefront to save big on lookalikes for your favorite brands, including Lilly Pulitzer, Tuckernuck, Bogg, Mackenzie Childs, and Queen of Sparkles.

 

Wrap-Up

Happy shopping for preppy dresses: Amazon edition!

XOXO – Katie <3

The Ultimate Style Guide To Preppy Clothes (2026 Edition)

***Please note that this The Ultimate Style Guide To Preppy Clothes will be updated and recirculated periodically to reflect the most up-to-date information. This shopping guide was most recently updated as of July 2026.***

Calling all fellow preppy fashion enthusiasts! This style guide to preppy clothes will map out the preppy fashion style and what it truly means to be preppy! If you love grandmillennial style clothing, then check out my where to buy grandmillennial style clothing guide.

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page.

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

The Ultimate Style Guide To Preppy Clothes (2026 Edition)

Looking for ways to save on your favorite preppy brands?!?! Be sure to check out my Poshmark which is updated weekly with the latest & greatest secondhand preppy deals!

 

Table of Contents

What Is Preppy Style?!

Preppy Fashion Inspiration: From The Screen To The Streets

Preppy Wardrobe Essentials + Key Staples

Preppy Style Variations

Seasonal Preppy Outfit Inspiration

Preppy Clothes Fit For Every Occasion

Preppy Accessories 

Where To Shop For Preppy Clothes

What Is Preppy Style?! 

Preppy Style is a classic, all-American aesthetic that is rooted in the collegiate traditions of the East Coast Ivy League colleges and prep schools of the 20th century. Preppy Style blends refined classic sophistication with youthful, sporty elements, incorporating structured silhouettes, bright + pastel colors, textured fabrics such as Tweed and cable-knit, and wardrobe staples like loafers, oxford shirts, and blazers. 

All-things preppy style saw a resurgence in the 1980’s thanks to satirical The Official Preppy Handbook – published by Lisa Birnbach. In the late 2000’s, preppy style got a modern-day spin – headbands and pleated Mini skirts and all – thanks to shows like Gossip Girl. Today, preppy style remains popular worldwide from both trendsetters and lifelong preppy style lovers, alike.

Preppy Fashion Inspiration: From The Screen To The Streets

Preppy fashion has taken the stage from gracing our screens to inspiring us in our everyday life on the streets (and social media!). As a proud preppy fashion enthusiast, these are some of the most iconic preppy fashion moments in popular culture (in my opinion!):

  • Blair Waldorf in Gossip Girl – the headbands, Upper East Side elegance, and private school preppy style with lunch on The Met steps clad in blazers and pleated skirts, OH MY!
  • The Kentucky Derby – clad in iconic fascinators, all-things seersucker, pastels, bows, and more with a Mint Julep in-hand at Churchill Downs in Louisville, the Kentucky Derby’s fashion is truly a preppy fashion galore!
  • The Pink Retreat – Lilly Pulitzer lover’s annual Palm Beach Retreat aka a conference and retreat for everyone who LOVES the bubbly and sunshine-inspired preppy fashion brand to come together and share their love of Lilly Pulitzer.
  • Everyday Life – Everyday, whether I am running errands, going out to brunch or dinner, or traveling, I always run into a fellow preppy fashion enthusiast and feel nothing short of inspired! Truly, I find the everyday preppy fashion lovers to be my favorite source of inspiration for styling Preppy clothes!!

Preppy Wardrobe Essentials + Key Staples

Whether it be a blazer, Oxford button down, trench coat, pair of pearl earrings, cable-knit sweater, or a timeless pair of flats, there are several preppy wardrobe essentials that every enthusiast probably has (or should have!). Indeed, I outline preppy wardrobe essentials and provide some outfit inspiration in my Styling Preppy Outfits Guide. 

Preppy Style Variations

Preppy style isn’t a one-size fits all style! Here are a few of the widely-known preppy style variations to keep in mind and draw inspiration from:

  • Preppy Core – Preppy Core takes the essential elements of preppy style and amplifies them for a more intentional, curated preppy vibe. Preppy Core places an emphasis on creating cohesive, highly styled looks that are unmistakably preppy.
  • Soft Preppy – Soft preppy embraces feminine, romantic elements within the preppy framework. This vibe features pastel colors, delicate fabrics, eyelet details, and flowing silhouettes. It’s perfect for those who want a gentler, more whimsical take on the traditional, Ivy League preppy aesthetic.
  • Old Money Aesthetic – The Old Money Aesthetic represents understated luxury and timeless elegance with a focus on high-quality fabrics, impeccable tailoring, neutral color palettes, and minimal branding. It’s all about looking effortlessly expensive without being flashy.
  • Y2K Preppy – Y2K Preppy draws inspiration from early 2000’s fashion icons from popular movies and shows like Clueless and Gossip Girl. Y2K Preppy incorporates nostalgic elements like mini skirts, crop tops, bold pink tones, and playful accessories. This style appeals to those who love the youthful and fun energy of 2000’s fashion.
  • Modern Preppy (or “new preppy”) – Modern preppy takes traditional elements and updates them with the current time’s contemporary trends, bolder colors, and more relaxed silhouettes. This style embraces the fashion of the current time while maintaining preppy’s polished aesthetic.
  • Classic Preppy (also known as “OG preppy” or “old preppy”) – Classic preppy remains true to its traditional Ivy League roots with conservative cuts, traditional patterns like argyle and plaid, and a refined color palette of navy, white, khaki, and burgundy. Think timeless pieces that could have been worn decades ago and still look current today.

While there are plenty of preppy style variations widely-known amongst fellow preppy fashion lovers, most importantly, it is key to dress in a way that is true to you. Make your preppy style yours and only yours.

Seasonal Preppy Outfit Inspiration

There are so many fun ways to style preppy clothes all-year-round! My Cute Preppy Outfits page is my personal archive where I share ALLL of my preppy outfits throughout the years. I also have a Styling Preppy Outfits guide that I highly suggest checking out as a fellow preppy.

Spring/Summer Preppy Outfits

For all-things Spring/Summer Preppy Outfits, be sure to check out my 50+ Summer Preppy Outfits guide for ALLLLL the Summer preppy style inspiration. Also, check out these Spring/Summer preppy clothing essentials.

 

Fall/Winter Preppy Outfits 

For all-things Fall/Winter Preppy Outfits, be sure to check out my 50+ Fall Preppy Outfits guide for ALLLLL the Fall preppy style inspiration. Also, check out these Fall/Winter preppy clothing essentials.

 

Preppy Clothes Fit For Every Occasion

We all have a ton of events on our calendars throughout the year and there are some preppy clothes fit for every occasion. One of the best things about preppy clothes is that they are versatile and, when styled appropriately, can be worn for multiple occasions. That all being said, here are a few occasions and style inspiration:

  • Business Casual Work Days – Shift dresses in solid colors or business casual-appropriate patterns including Tweed, plaid, or when styled appropriately Lilly Pulitzer shifts and paired with a cardigan/Tailored blazer of pair of ballet flats. Other options include a blouse/cashmere sweater and pants as well as a midi skirt with a tucked-in blouse. Ah, the options are endless when styled appropriately to your workplace’s dress code.
  • Lazy Days – Love me a two-piece lounge set like some of these on Amazon as well as a skort or jeans and a tee/Crewneck Sweatshirt. But, nothing beats a nice pair of pajamas for lounging around the house or for simple errands!
  • Holiday Events – Tartan IS your best friend throughout the holiday season, as well as all-things shimmer and sparkle and glitter in blouses, skirts, dresses, and more!
  • Preppy Dinner Outfit – Style an elegant shift dress, midi dress, or Maxi Dress with a pair of heels and accent jewelry and add a fun clutch or novelty bags for an extra fun flair!
  • Valentine’s Day & Galentine’s Events – Whether for date night or for a night with the Galentine’s, opt for all-things red and pink and anything with hearts on it for all-things Valentine’s.
  • Easter – Opt for a pastel-colored dress with pops of bright colors such as yellow or pink, perhaps with a scalloped hemline or ric-rac on the hemline. Pair with your favorite cardigan. 
  • Church – Nothing beats pairing one of your favorite dresses or skirts/blouses with *none other than* a tailored blazer or cardigan!

& the list could go on and on and on! There are indeed several events that we all have on our calendars – many of which we can use what we have in our closets multiple times! 

Preppy Accessories 

There are several fun preppy accessories to choose from, whether it be a timeless leather tote or crossbody bag, anything monogrammed, a headband, a ball cap, or a canvas boat tote – my favorite being from either LL Bean or Lands’ End. 

Preppy Bags

Preppy Scarves

 

Preppy Jewelry 

 

Preppy Shoes

 

Preppy Pouches 

 

Preppy Hats & Headbands

 

Where To Shop For Preppy Clothes

There are several places to shop for preppy clothes, whether it be at your local department store or Target or Walmart, on Amazon, a small business, thrift store, or several shops. In fact, I have a preppy brands guide where I list several popular preppy clothing brands that fellow preppy fashion enthusiasts like myself shop at – many of which you can find on Amazon, at department stores, thrift stores, or online. 

For more preppy brands inspiration, including brands like Boden, brands like Sezane, brands like Ralph Lauren, brands like Tommy Bahama, stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck guides. If you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer (or brands like it), then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales. And if you’re into luxury fashion for less, than check out my brands like Louis Vuitton guide.

Where To Sustainably Shop For Preppy Clothes

There are several spots to sustainably shop for preppy clothes, whether in-store or online. Within what I call home aka Northern Virginia, I’ve listed out several thrift stores in the region – many of which will likely have locations close to your home, too. 

Looking for ways to save on your favorite preppy brands?!?! Be sure to check out my Poshmark which is updated weekly with the latest & greatest secondhand preppy deals!

 

For online secondhand shopping alongside Poshmark, I highly recommend the following:

  • eBay
  • Vinted
  • ThredUp
  • Depop
  • Mercari

Above all else, when shopping for preppy clothing, I highly suggest looking for coveted preppy brands that many of us Preppies have loved and supported over the years – whether brand-new or secondhand (I have done and continue to do both!). 

Wrap-Up

As a proud forever preppy fashion lover, I feel beyond proud to identify as a “preppy,” which is a style that never truly goes out of style. I hope this guide to styling preppy clothes helps you feel the same as a preppy fashion lover, too!

XOXO – Katie <3

The Ultimate Guide To Styling Preppy Outfits (2026 Edition)

***Please note that this The Ultimate Guide To Styling Preppy Outfits will be updated and recirculated periodically to reflect the most up-to-date information. This shopping guide was most recently updated as of July 2026.***

If you’re like me and a mega preppy style enthusiast, then this guide to styling your next best preppy look is for YOU!

*Disclaimer: Please note that this post contains affiliate links, which means that if you purchase through one of my links, then I will receive a small commission. This commission is at no extra cost to you. Additionally, this post is not sponsored, and all opinions are my own.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page.

Interested in getting the latest scoop on all the preppy + grand millennial fashion and decor (& more!) deals?!?! Be sure to join in on the fun over on Substack!

The Ultimate Guide To Styling Preppy Outfits (2026 Edition)

Table of Contents

Introduction To Preppy Style & Its Modern Evolution

Essential Pieces + Foundational Items To Your Preppy Wardrobe

Preppy Outfits For School: A Complete Style Guide

Seasonal Preppy Outfit Ideas: Summer and Fall Styling

Preppy Footwear Guide: All-Things Shoes

Preppy Accessories: Bags, Jewelry, & More

Preppy Shopping Guide – Brands + Stores

Preppy On A Budget Tips

Introduction To Preppy Style & Its Modern Evolution

What is Preppy Style?! 

Preppy Style is a classic, all-American aesthetic that is rooted in the collegiate traditions of the East Coast Ivy League colleges and prep schools of the 20th century. Preppy Style blends refined classic sophistication with youthful, sporty elements, incorporating structured silhouettes, bright + pastel colors, textured fabrics such as Tweed and cable-knit, and wardrobe staples like loafers, oxford shirts, and blazers. 

All-things preppy style saw a resurgence in the 1980’s thanks to satirical The Official Preppy Handbook – published by Lisa Birnbach. In the late 2000’s, preppy style got a modern-day spin – headbands and pleated Mini skirts and all – thanks to shows like Gossip Girl. Today, preppy style remains popular worldwide from both trendsetters and lifelong preppy style lovers, alike.

Essential Pieces + Foundational Items To Your Preppy Wardrobe

Creating the perfect preppy Wardrobe begins with foundational pieces that offer maximum versatility. These carefully curated items work together seamlessly, allowing you to transition them effortlessly from classroom to boardroom to coffee shop to evening activities and everything in between.

It’s important to note that your preppy must-haves may differ from my own preppy must-haves. Everyone’s style, while preppy, is extremely uniquely yours and only yours. 

Here are some of the many preppy staples I think can be foundational for anyone’s very own preppy Wardrobe:

  • Plaid skirts
  • Blazers
  • Button downs
  • Skorts
  • Cable-knit sweaters 
  • American flag sweaters
  • Gold or silver accent jewelry
  • Blue jeans 
  • Little Black Dresses
  • Cardigans 
  • Tweed dresses (or really anything Tweed)
  • Shift dresses 
  • Striped tees
  • Knit tees
  • Shirt dresses
  • Fair Isle sweaters
  • Cashmere 
  • Trench coats

One of the most beautiful things about preppy staples is that they are versatile. Each of these pieces can be combined with layering, creating looks that are both fashionable and functional while also timeless. You can easily mix and match these items to create preppy outfits suitable for any occasion. 

Preppy Outfits For School: A Complete Style Guide

Although I am not in school anymore, school is truly the perfect backdrop to showcase your preppy outfits while maintaining practicality and comfort throughout the day. Whether you’re planning your back-to-school wardrobe or looking for fresh OOTD inspiration, these preppy looks will keep you both polished and confident as you strut down the halls.

You can create effortlessly chic looks that take you from the first period to after-school activities and everything in between:

  • Personalized + Practical Backpack – Your signature bag at school is none other than your backpack, why not personalize it to be uniquely yours?!
  • Simple Preppy Combinations – Pair a tennis skirt with a fitted long-sleeve top and sneakers for comfortable, trendy style
  • Casual Preppy Basics – Combine athletic-inspired pieces like hoodies or sweatshirts with pleated skirts for the perfect balance of comfort and polish
  • Non-Jean Alternatives – Explore skorts, athletic shorts, and skirts for fresh takes on everyday school style
  • Lazy Day Aesthetics – Cute while still comfortable outfits that feature soft fabrics and relaxed silhouettes that still look intentional

Special School Events and Spirit Week

Picture Day Perfection

Choose timeless pieces in flattering colors – think classic pink and white combinations or plaid patterns that photograph beautifully and won’t look dated in years to come.

Preppy Spirit Week Ideas

  • Pajama Day – Elevate the concept with preppy PJ sets in coordinating colors and patterns, look to brands such as Printfresh, Roller Rabbit, and Joyspun at Walmart to rock the look in true preppy fashion.

 

  • Last Day of School – Celebrate in style with your favorite preppy summer outfit featuring bright colors and comfortable fabrics, look to brands such as Lilly Pulitzer, J Crew Factory, or Crown & Ivy at Belk to rock the look in true preppy Summer fashion. 

Seasonal Preppy Outfit Ideas: Summer and Fall Styling

One of the best parts about preppy fashion?!?! Preppy fashion adapts beautifully to every season, each of which brings its own color palettes, fabrics, and *of course* styling opportunities. Master the art of seasonal dressing while maintaining your signature preppy aesthetic. 

Preppy Essentials For Summer Outfits 

 

Preppy Essentials For Fall Outfits 

 

For more Summer & Fall Preppy Outfit inspiration, look no further than my 50+ Preppy Summer Outfits and 50+ Preppy Fall Outfits curations for more style inspiration. For year-round preppy outfit ideas, then look no further than my Cute Preppy Outfits page, which contains an archive of my monthly preppy outfits recaps.

Preppy Footwear Guide: All-Things Shoes

The right footwear will elevate any preppy outfit from good to great. Preppy style embraces classic footwear with an element of comfort and practicality. Whether it be a pair of ballet flats or riding boots or sneakers, any and every preppy outfit will be made uniquely yours with the perfect pair of shoes.

 

For more inspiration on preppy brands to shop for your preppy outfits including footwear, look no further than my preppy brands guide.

Preppy Accessories: Bags, Jewelry, & More

Bags, jewelry, scarves, and pouches, OH MY! One of the best ways to take your preppy outfits to the next level is with none other than accessories. Accessories are the finishing touches which transform good outfits into great ones. In true preppy fashion accessories of all kinds serve both functional and aesthetic purposes, which combines practicality with timeless style.

Preppy Bags 

 

Preppy Jewelry

Preppy Scarves 

Preppy Pouches 

For more inspiration on preppy brands to shop for your preppy outfits including accessories, look no further than my preppy brands guide. 

Preppy Shopping Guide – Brands + Stores

There are a ton of brands and stores which embody preppy style. In fact, I have a full list of preppy brands that I’ve supported, admired, and adored over the years as a lifelong preppy. 

Off of the top of my head, here are some of my favorite preppy brands to shop at:

  • Brooks Brothers
  • Crown & Ivy at Belk
  • J Crew/J Crew Factory
  • Kate Spade New York
  • Lands End
  • Lilly Pulitzer 
  • LL Bean
  • Ralph Lauren
  • Southern Tide 
  • Talbots
  • Tommy Hilfiger
  • Tory Burch
  • Tuckernuck
  • Vineyard Vines

If you’re like me and also a forever preppy style enthusiast, then check out my brand guides, including stores like Williams Sonoma, brands like Ted Baker, stores like ban.do, stores like Kohl’s, brands like Vera Bradley, brands like Betsey Johnson, brands like Southern Tide, brands like Vineyard Vines, brands like Tory Burch, brands like Farm Rio, brands like J Crew, brands like Banana Republic, brands like Talbots, brands like Kate Spade, and brands like Ann Taylor, such as Lilly Pulitzer and Tuckernuck, then be sure to check out my brands like Lilly Pulitzer and brands like Tuckernuck guides.

For more inspiration on preppy brands to shop for your preppy outfits including accessories, look no further than my preppy brands guide. 

Preppy On A Budget Tips

If you are looking to find ways to save on gorgeous preppy pieces from Lilly Pulitzer, then check out Lilly Pulitzer’s semi-annual Sunshine Sale and Black Friday/Cyber Monday deals, my list of Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, as well as other brands that are mentioned’s sales.

For more preppy and grand millennial deals and steals for less, check out my Amazon Storefront to save big on lookalikes for your favorite brands, including Lilly Pulitzer, Tuckernuck, Mackenzie Childs, Queen of Sparkles, and Bogg.

If you’re interested in secondhand shopping, then I recommend checking out sites like ThredUp or Poshmark for some online thrifting scores. If you LOVE thrifting in real life, then check out your local thrift store for preppy brands and preppy staples.

Wrap-Up

From bright printed shift dresses to timeless blazers and all-things cashmere and Tartan and everything in between, preppy outfits truly incorporate so many timeless and sometimes trendy wardrobe staples. As a forever preppy fashion lover, I feel beyond proud to identify with as a “preppy,” which is a style that never truly goes out of style. I hope this guide helps you feel the same as a preppy fashion lover, too!

XOXO – Katie <3