Your Guide To The Best Dog-Friendly Wineries in Northern Virginia (2026 Edition)

***Please note that this Your Guide To The Best Dog-Friendly Wineries in Northern Virginia (2026 Edition) travel guide will be updated and recirculated periodically to reflect the most up-to-date Virginia Wine scene. This guide was most recently updated as of October 2026.***

If you’re like me and you want to bring your four-legged friends with you everywhere you go, then YOU’RE IN LUCK: this guide outlines the best dog-friendly wineries in Northern Virginia! Each of these dog-friendly wineries in Northern Virginia outlined in this guide have been visited by me, personally, to ensure that they’re safe, welcoming, and wonderful places to bring your dog.

For more United States travel inspiration, check out my Exploring 50 States expedition page. For more Washington, DC area travel inspiration, check out my Exploring The DMV page.

Your Guide To The Best Dog-Friendly Wineries in Northern Virginia (2026 Edition)

For more Northern Virginia picks from a Northern Virginia local, look no further than these guides to garden centers, things to do, pumpkin patches, parks, and thrift stores in the region. To plan your ultimate Northern Virginia wine tour, then look no further than Cork & Keg Wine Tours as well as a local’s guide to Northern Virginia Wineries! For dining options in Northern Virginia, look no further than these Old Town Alexandria dining, brunch, wine bar, and cafes guides as well as this Arlington wine bars guide, Burke restaurants guide, and Fairfax brunch guide. 

Table of Contents

A Way To Save at Northern Virginia Wineries

Dog-Friendly Northern Virginia Wineries

A Way To Save at Northern Virginia Wineries

Download Reserve Pass and sign up for YOUR membership today!! Reserve Pass is currently the only app in the United States that is essentially a nationwide wine (and sometimes beer) tasting pass for you and a guest (see more here)! Memberships are available in monthly and annual formats.

The key features of Reserve Pass are:

  • Explore – by simply downloading the Reserve Pass app, you can simply plan your wine tasting adventure within your own backyard or while on vacation.
  • Perks – as a Reserve Pass member, you get to enjoy exclusive perks while touring historical sites, strolling through vineyards, and tasting local wines.
  • Revisit – unlike just any old coupon, you can revisit any of the wineries you loved and get the same Reserve Pass deals with them time and time again.

Interested in getting your own Reserve Pass today?! Interested in trying Reserve Pass for yourself?!?! Use my discount code “ktwine40” for 40% off an annual membership today (value: $69).

For more details on Reserve Pass, look no further than here.

Dog-Friendly Wineries in Northern Virginia

868 Estate Vineyards

Address: 14001 Harpers Ferry Road, Purcellville

About: Dating back to 2012 when 3 families – Peter and Nancy Deliso, Wendy and Chris Charron, and Carl and Erin DiManno – came together to create a place where communities can come together and enjoy events, savor a glass of wine, and simply be together. Today, that place is 868 Estate Vineyards!

8 Chains North Winery

Address: 38593 Daymont Lane, Waterford

About: 8 Chains North Winery is a working farm, event venue, winery, and brewery near Leesburg, Virginia that gets is name from the first vineyard on its grounds that were used as a Civil War Crossing known as 8 Chains. This farm, event venue, winery, and brewery is also extremely dog-friendly with a fenced area for your four-legged friends to run around at while you savor a glass of wine.

Barrel Oak Winery and Brewery

Address: 3623 Grove Lane, Delaplane

About: Also known as “BOW”, Barrel Oak Winery and Brewery values itself on passion, commitment, and fine wine as well as a friendly place for everyone to bring your dog both indoors and outdoors. Everyone truly feels right at home at Barrel Oak Winery and Brewery, whether human or canine!

Blue Valley Vineyard and Winery

Address: 5535 Blue Valley Way, Delaplane

About: With Greek mountainside roots in winemaking, the Zissios family brought a piece of Greece to Northern Virginia through opening Blue Valley Vineyard and Winery in the Shenandoah Valley to the public in 2015. To this day, Blue Valley Vineyard and Winery is still family-owned and runs on the Greek value of respect, ensuring that everyone who walks through its doors are treated like family.

Casanel Vineyards & Winery

Address: 17952 and 17956 Canby Road, Leesburg

About: Shaped in their three core values of people, passion, and a sense of place, owners Casey and Nelson DeSouza planted their roots at what is now Casanel Vineyards & Winery in 2006. With a lot of hard work, authenticity, and a  whole lot of celebration, the DeSouza’s have created a place where everyone can come together no matter who they are for a glass of wine (or a mocktail) and leave having a great time. Today, the values of people, passion, and a sense of place still reign true at Casanel as the winery has several offerings to enjoy whether it be enjoying a glass or flight in their tasting room or outside at their patio or balcony, or a stroll around the grounds’ gazebo, everyone will be sure to have a great time!

Paradise Springs Winery

Address: 13219 Yates Ford Road, Clifton

About: One of the closest wineries to Washington, DC, Paradise Springs Winery is a bicoastal winery with a location in Santa Barbara, California as well as in Clifton, Virginia. Guests can enjoy the winery’s gorgeous grounds and scenery in the heart of Clifton, Virginia as well as different food trucks that come to visit.

Potomac Point Winery & Vineyard

Address: 275 Decatur Road, Stafford

About: Located in Stafford County with an onsite bistro, Potomac Point Winery & Vineyard offers an elegant twist to the vineyard experience. Be sure to indulge in a delicious meal and one of their wine-soaked cakes at their onsite bistro and take in all of the lovely scenic views.

Three Fox Vineyards & Brewery

Address: 10100 Three Fox Lane, Delaplane

About: A family and dog-friendly winery and brewery with a pizza shed overlooking the Shenandoah mountains, Three Fox Vineyards & Brewery is a welcoming place for everyone to enjoy a fun vineyard outing. Be sure to check out the beautiful onsite meadow and creek – perfect for kids and dogs to soak in some sunshine – and enjoy some wine at one of their tables in the vines! Read my full review on Three Fox Vineyards & Brewery here.

Twin Oaks Tavern Winery

Address: 18035 Raven Rocks Road, Bluemont

About: Twin Oaks Tavern Winery is a two-generation, woman-owned winery on the foothill of the Shenandoah mountains. Located in the Bear’s Den Historic District, Twin Oaks Tavern is one of many stone houses built from 1890-1920 and was transformed into a winery in 1999 after a fire burned much of its original structure down in the 1980s. Today, Twin Oaks Tavern Winery is a welcoming place that’s also dog-friendly.

 

Wrap-Up

Personally, I feel that dogs make everything better, especially when they can visit our favorite Northern Virginia wineries with us!

XOXO – Katie <3

The Best Gifts For Cocktail Lovers From A Fellow Cocktail Lover (2026 Edition)

***Please note that this The Best Gifts For Cocktail Lovers From A Fellow Cocktail Lover (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.***

Being a Cocktail Lover myself, I’ve curated the Best gifts for Cocktail Lovers, from glasses to recipe books to bartender sets and *just about* everything in between!

*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 Gifts For Cocktail Lovers From A Fellow Cocktail Lover (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as where to buy the best hostess gifts under $30, 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 Hostess Gifts Under $30, best stationary lovers gifts, 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 Gifts For Cocktail Lovers From A Fellow Cocktail Lover (2026 Edition)

Honestly, I feel SOOOO tempted to order some of these gifts for cocktail lovers as a fellow cocktail lover, myself! I’ve used some of the glasses within this gift guide, and they are a cherished part of my collection, BUT I think that that Pink Dirty Martini candle *IS* calling my name!!

 Wrap-Up

Let’s raise a cocktail to celebrating and cherishing the cocktail lovers in our lives!

XOXO – Katie <3

The Best Hostess Gifts Under $30 From A Lifelong Hostess (2026 Edition)

**Please note that this The Best Hostess Gifts Under $30 From A Lifelong Hostess (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 lifelong hostess, I have curated some of the Best Hostess Gifts Under $30, making them a budget-friendly way to celebrate those who bring us together.

*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 Hostess Gifts Under $30 From A Lifelong Hostess (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as where to buy the best hostess gifts under $30, 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 stationary lovers gifts, 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 Hostess Gifts Under $30 From A Lifelong Hostess (2026 Edition)

From tried and true products I’ve used and loved myself (as a lifelong hostess!) to some best sellers loved by many of y’all aka my readers, these are some of the best Hostess Gifts that retail for under $30!

 

Wrap-Up

Let’s raise a glass to treating the hostess with the mostess in YOUR life!

XOXO – Katie <3

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

The Best Beach Lover Gifts From Someone Who Loves The Beach (2026 Edition)

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

As someone who loves the beach and has tons of family and friends who do too, I have curated some of the best Beach Lover Gifts 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 Beach Lover Gifts From Someone Who Loves The Beach (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling beach 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 history lover 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 preppy gift ideas, 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 Beach Lover Gifts From Someone Who Loves The Beach (2026 Edition)

 

Wrap-Up

Let’s raise a glass by the beach *of course* to treating the fellow beach lovers in your life!

XOXO – Katie <3

The Best Travel Gifts From A Fellow Globetrotter (2026 Edition)

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

As a Globetrotter who has traveled to several different countries, some of my favorite gifts to receive are travel gifts! That all being said, I’ve curated some of the best travel gifts I’ve personally received and the fellow Globetrotters in your life will love, too.

*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 Travel Gifts From A Fellow Globetrotter (2026 Edition)

More Preppy Shopping Guides You Will Love

If you also love preppy clothing brands such as those selling travel 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 travel 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.

or 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 lovers 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 Travel Gifts From A Fellow Globetrotter (2026 Edition)

 

Wrap-Up

Let’s raise a glass to treating the fellow travelers in YOUR life!

XOXO – Katie <3

The Best Gifts For The History Lover From A Fellow History Lover (2026 Edition)

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

As a fellow History lover (and self-proclaimed History nerd!), I’ve curated some of the best history lover gifts for your loved ones! From unique history-themed mail subscriptions, books, glassware, and more, these unique history lovers gifts are sure to leave a lasting impression on the history nerds 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. 

The Best Gifts For The History Lover From A Fellow History Lover (2026 Edition)

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 Gifts For The History Lover

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.

Lilly Pulitzer Sales, Dupes & Affordable Alternatives

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.

More Preppy Style Inspiration

For *even* more preppy style inspiration including history lover 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.

More Gift Guides You’ll Love

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 travel gifts, best Beach 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.

Travel Essentials & eSIMs

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 Gifts For The History Lover From A Fellow History Lover (2026 Edition)

 

Wrap-Up

Here’s to treating the history lovers in YOUR life!

XOXO – Katie <3

The Best Gifts For Flower Lovers From A Flower Lover (2026 Edition)

***Please note that this The Best Gifts For Flower Lovers From A Flower Lover (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.***

As someone whose a fellow flower lover (maybe I have to thank the fact that I was born in May for this!), I have found some of the best gifts for Flower Lovers in your life – whether it be a mug, candle, or wine glass. Each of these gifts for flower lovers will truly be something that they will cherish and appreciate. 

*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. 

The Best Gifts For Flower Lovers From A Flower Lover (2026 Edition)

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 Gifts For Flower Lovers From A Flower Lover

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.

Lilly Pulitzer Sales, Dupes & Affordable Alternatives

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.

More Preppy Style Inspiration

For *even* more preppy style inspiration including flower lovers 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.

More Gift Guides You’ll Love

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, travel gifts, history lover 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.

Travel Essentials & eSIMs

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 Gifts For Flower Lovers (2026 Edition)

 

Wrap-Up

Here’s to treating the flower lovers in YOUR life!

XOXO – Katie <3

Preppy Outfits Diaries – September 2026

September started off strong with landing in Glasgow, Scotland for a chilly week that was the ultimate Sweater Weather preview and also ended on a chilly note with Sweater Weather in the Washington, DC area and crushing my professional goals as well as hosting 2 Fall Dinner parties. Truly, I feel so grateful for September 2026 and enjoyed wearing SOOO many fun Fall preppy outfits to commemorate the start of the season!

*Disclaimer: Please note that this page 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. Thank you for supporting The Pink Chickadee.*

For more preppy style & grand millennial home content, check out my Preppy Fashion & Grand Millennial Home page. For my outfit archive, look no further than My Preppy Outfits Archive.

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!

   

Preppy Outfits Diaries – September 2026

My Favorite Pieces

Whether it be feeling ultra-confident in the hottest floral jacket of the season to run errands, snuggling up in my favorite two-piece knit sweater-skirt set, or taking my favorite vegan leather bag on the town, my preppy outfits this past September truly lived up to the hype and found myself gravitating towards the same staples again and again!

This month, I decided to do something a bit different and share some of my favorite pieces that I used with some of my favorite preppy outfits, including a blanket and some newly-purchased wine glasses.

 

My Outfits

midi dress with a green and red floral block print, puff sleeves, and a tied waist - Preppy Outfits

pink long-sleeve pullover and matching scalloped skort set

black-and-white striped long-sleeve top paired with relaxed light-wash barrel-leg jeans and black flats - Preppy Outfits

a green floral print smocked-waist poplin midi dress paired with a canvas tote bag

Umgee Floral Midi Dress With Ruffle Trim And Elastic Waist

Willa Midi Dress in Mountain Bluebird from J.Crew Factory - Preppy Outfits

purple striped long-sleeve shirt, dark skirt, black knee-high boots, and Louis Vuitton monogram tote bag

navy blue sweater, paired with black leggings and dark tall rain boots - Preppy Outfits

white long-sleeve dress paired with a pink plaid scarf and dark tall rain boots

black-and-white floral jacket, pink pants, and a brown monogram tote bag

black mini dress paired with a patterned neck scarf

The Ellie Nap Dress by Hill House Home - Preppy Outfits

beige scalloped-edge trench coat over green gingham pants

the Bagheera - Now or Later Skirt in Hot Pink by Printfresh - Preppy Outfits

pink floral Lilly Pulitzer top and gold jewelry

pink short-sleeve tweed dress paired with tall black rain boots

bright pink button-front jacket paired with tall black rain boots and Monogram canvas tote bag - Preppy Outfits

floral print zip-up jacket paired with a black midi skirt and bright pink handbag

quilted puffer vest over a cream sweater, magenta pants, tall black rain boots, and a Louis Vuitton Neverfull MM monogram tote bag

floral blouse paired with light-colored, wide-leg satin trousers - Preppy Outfits

Lilly Pulitzer maxi dress with a wrap skirt and white lace trim

 pink plaid tunic paired with classic tall black boots - Preppy Outfits

checked oversized jacket with a vibrant magenta top and matching trousers

pink Lilly Pulitzer Pollie Midi Dress -Preppy Outfits

Wrap-Up

Here’s to styling some more outfits into the Sweater Weather months (and beyond!)!

XOXO – Katie <3