July 2026 - Page 3 of 3 - The Pink Chickadee

30 Brands Like Vineyard Vines For A Preppy Vibe

***Please note that this 30 Brands like Vineyard Vines 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 July 2026.***

My family has been and will likely always be Vineyard Vines fans! In high school, I was really into preppy tees and the several brands like Vineyard Vines that sell them (as well as their iconic Shep Shirts aka their pullovers!). While I don’t wear preppy tees as much anymore, I do adore the several brands like Vineyard Vines that I still wear to this day as a forever preppy fashion lover.

If you’re like me and also love other popular brands like Vineyard Vines, including 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.

*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!

30 Brands Like Vineyard Vines For A Preppy Vibe

1 – 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.

2 – 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.

3 – 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.

4 – 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.

5 – Crown & Ivy at Belk

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

6 – 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.

7 – Kiel James Patrick

Made in the USA, Kiel James Patrick was founded in 2009 when the designer started making handcrafted rope and anchor bracelets. Since then, the fashion brand that proudly gives off all-things New England vibes has expanded into men’s and women’s apparel while Kiel James Patrick and his wife Sarah Vickers maintain a strong social media presence. Shop Kiel James Patrick here.

8 – 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.

9 – 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.

10 – Southern Marsh

Headquartered in Baton Rouge, Louisiana, Southern Marsh – proudly known as the original Southern outfitter – is well-known for their tees, pullovers, shorts, and more inspired by none other than the Southern Marsh. Shop Southern Marsh here.

11 – 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.

12 – 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.

13 – 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.

14 – Brooks Brothers

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

15 – Lacoste

Founded in 1933 by tennis legend René Lacoste and textile manufacturer André Gillier. Lacoste is a premier French fashion and sportswear brand playing tribute to Lacoste’s nickname “The Crocodile” in the 1920’s by the American Sports Press, which remains the brand’s well-known logo. Shop Lacoste here.

16 – 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.

17 – Tommy Hilfiger

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

18 – 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.

19 – 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. The brand has a UPF 50+ rating, to ensure you feel great while looking it, too. Shop Cabana Life here.

20 – Chaps

Owned by the Ralph Lauren Corporation and founded in 1978, Chaps operates as a budget-friendly preppy lifestyle brand (one of many preppy brands in this list!) to its sister brand Ralph Lauren. Shop Chaps at Belk here.

21 – Charter Club at Macy’s

Known for its preppy women’s apparel especially their cashmere products, Charter Club is a private label brand at Macy’s that offers all-things preppy for women at an affordable and accessible price point. Shop Charter Club here.

22 – 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.

23 – 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.

24 – 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.

25 – 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.

26 – 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.

27 – 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.

28 – Tommy Bahama

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

29 – 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.

30 – 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.

Wrap-Up

Happy Shopping, fellow Vineyard Vines fans!!!

XOXO – Katie <3

thepinkchickadee3 Comments

20 Brands Like Tory Burch For Bags, Shoes, Clothing, & More

***Please note that this 20 Brands Like Tory Burch 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 July 2026.***

Tory Burch is a well-loved contemporary fashion brand known for its bags, shoes, clothing, and more. If you’re like me and you LOVE Tory Burch, then you’ll love these 20 brands like Tory Burch, too.

If you’re like me and also love other popular brands like Tory Burch, including 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. Looking to save on gorgeous preppy pieces from Lilly Pulitzer or similar brands? Don’t miss 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 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!

20 Brands Like Tory Burch For Bags, Shoes, Clothing, & More

1 – 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.

2 – Coach

Starting in 1941 in a Manhattan loft as a family-run business with only six artisans, Coach has since grown into a renowned, American fashion house known for their popular handbags, premium leather craftsmanship, and accessories. Shop Coach here and the Coach Outlet here.

3 – Rebecca Minkoff

An American fashion brand founded in 2005 by brother-sister duo Uri and Rebecca Minkoff in New York City, Rebecca Minkoff has since become a popular accessible luxury fashion brand and is distributed in over 900 stores worldwide and has retail stores in cities such as New York City and Tokyo. Shop Rebecca Minkoff here.

4 – Ted Baker

Originally founded in Glasgow, Scotland in 1988 by Ray Kelvin who named the business after his alter ego, Ted Baker has since become a renowned British fashion and lifestyle brand known for its contemporary womenswear, menswear, accessories, and of course their distinct floral prints. Shop Ted Baker here.

5 – Alice + Olivia

Alice + Olivia was founded by Stacey Bendet in 2002 and is a New York City-based contemporary fashion and lifestyle brand worn by the likes of Jessica Alba, Gwyneth Paltrow, and Sarah Jessica Parker and known for its whimsical, vintage-inspired touches mixed with modern tailoring. Shop Alice + Olivia here.

6 – Michael Kors

Established in 1981 by Long Island-based designer and former Project Runway judge Michael Kors, Michael Kors is known for its jet-set glamour fashion including luxury ready-to-wear, handbags, and accessories globally. Shop Michael Kors here.

7 – Sezane

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

8 – Kurt Geiger

A popular British luxury accessories and footwear brand founded on London’s Bond Street in 1963, Kurt Geiger is known for its bright and bold designs at an accessible price point with its iconic eagle embellishments. Shop Kurt Geiger here.

9 – 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.

10 – Radley London

Dating back to 1998 when it was founded by Lowell Harder, Radley London is a luxury British accessories brand sold at an accessible price point with a signature Scottie dog mascot. Shop Radley London here.

11 – 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.

12 – 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.

13 – 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.

14 – Madewell

Started in 2006 as a premium denim brand for both men and women, Madewell strives to create pieces with the utmost high-quality craftsmanship fit to last a lifetime. Shop Madewell here.

15 – Tuckernuck

16 – 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.

17 – Ann Taylor

Since its 1954 founding, Ann Taylor has grown into an iconic American women’s fashion brand, known for elegant, timeless, and reliable work apparel and sportswear with a size-inclusive focus. Shop Ann Taylor here.

18 – Mango

A well-known global fast-fashion retailer with its beginning in 1984 in Barcelona, Spain. Mango focuses trend-driven, accessible clothing, accessories, and footwear for all with positioning in the high-street market. Shop Mango here.

19 – 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.

20 – Abercrombie & Fitch

Dating back to 1892 as an upscale sporting goods brand, Abercrombie & Fitch has since evolved into a size-inclusive global fashion brand for all focused on everyday life. Shop Abercrombie & Fitch here.

Wrap-Up

Happy Shopping, my fellow Tory Burch fans!!!

XOXO – Katie <3

thepinkchickadee5 Comments

20 Brands Like Farm Rio

***Please note that this 20 Brands Like Farm Rio shopping guide will be updated and recirculated periodically to reflect the most up-to-date information. This review was most recently updated as of June 2026.***

Known as Brazil’s beloved fashion brand with its fun tropical prints and more, Farm Rio has also become a well-loved brand in the United States (and beyond!). We all know that Farm Rio’s clothing can come at a hefty price tag! This shopping guide will share 20 brands like Farm Rio in hopes that you can discover a new-to-you brand and with a not-so hefty price tag!

If you’re like me and also love other popular brands like Farm Rio, including 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.

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!

20 Brands Like Farm Rio

1 – Chicwish

Chicwish is an online retailer known for its feminine, whimsical, and vintage-inspired styles including tulle skirts, 3D floral appliques, and chunky knits – all mostly with prices ranging from $50-$100. Shop Chicwish on Amazon here.

2 – Crown & Ivy at Belk

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

3 – 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.

4 – Johnny Was

Named for the classic 1976 Bob Marley song, Johnny Was was founded in Southern California in 1987 by Eli Levite and is well-known for its American and bohemian-chic styles. Shop Johnny Was here.

5 – 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.

6 – Mango

A well-known global fast-fashion retailer with its beginning in 1984 in Barcelona, Spain, Mango focuses trend-driven, accessible clothing, accessories, and footwear for all with positioning in the high-street market. Shop Mango here.

7 – 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.

8 – 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.

9 – 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.

10 – 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.

11 – 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.

12 – 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.

13 – Wenrine

Wenrine offers preppy dresses on Amazon inspired by Lilly Pulitzer’s signature style at a fraction of the price. Shop Wenrine here.

14 – Tuckernuck

15 – 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.

16 – 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.

17 – J.Marie Collections

Women owned and Dallas, Texas-based, J.Marie Collections sells custom designed pieces bringing bright pops of color to your wardrobe. Shop J.Marie Collections at Dillard’s here.

18 – English Factory

Selling beautiful styles, timeless classics, and must-have apparel, English Factory is a popular preppy retailer. Shop English Factory at Nordstrom here.

19 – 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.

20 – LOFT

Wrap-Up

Happy Shopping and browsing, Farm Rio fans!!!

XOXO – Katie <3

thepinkchickadee5 Comments

Master List: All Lilly Pulitzer Signature Stores (2026 Edition)

***Please note that this Master List: All Lilly Pulitzer Signature Stores (2026 Edition) blog post will be updated and recirculated periodically. This post has most recently been updated as of July 2026.***

One of the most excellent ways to support Lilly Pulitzer is to support one (or a few!) of its many Signature Stores – a small business that carries the resort wear brand we all know and love. Many Lilly Pulitzer Signature Stores are woman-owned and family-owned and each has an incredible story behind it (be sure to check out their websites!). Personally, I feel proud to have become friends with the 3 sisters who own and are behind The Lucky Knot in Alexandria, Virginia through supporting them over the years. Like The Lucky Knot, there are several Lilly Pulitzer Signature Stores to support – some of which will hopefully be close to your home.

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

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!

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!

Master List: All Lilly Pulitzer Signature Stores (2026 Edition)

For more Lilly Pulitzer content, look no further than my brands like Lilly Pulitzer, Lilly Pulitzer Dupes on Amazon, where to buy dresses like Lilly Pulitzer, and Lilly Pulitzer Sunshine Sale prediction guides.

Department Stores That Carry Lilly Pulitzer

While not every city and state has a Lilly Pulitzer Signature Store to call home, there are multiple department stores – many of which have well-known e-Commerce platforms and occasional markdowns – to shop at.

Pink Chickadee shopping in a Lilly Pulitzer store

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 Lilly Pulitzer at 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 Lilly Pulitzer at Dillard’s here.

Nordstrom/Nordstrom Rack

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. Alongside Nordstrom, Nordstrom has its popular outlet sister store Nordstrom Rack (which also sells Lilly Pulitzer!).

Shop Lilly Pulitzer at Nordstrom here. Shop Lilly Pulitzer at Nordstrom Rack here.

Von Maur

A mid-to-high-end department store with its headquarters in Davenport, Iowa, Von Maur has multiple locations primarily in the United States Midwest selling well-known brands including Lilly Pulitzer.

Shop Lilly Pulitzer at Von Maur here.

Lilly Pulitzer Signature Stores

If you’re not local to one of the many Lilly Pulitzer Signature Stores listed in this guide, then don’t fret! Many of these shops have an online platform and may offer shipping – especially during the Sunshine Sale. I also recommend following any store(s) of interest on their Facebook or Instagram as they will offer shopping opportunities and share the most up-to-date information on any current markdowns and promotions.

The Pink Crab, a Lilly Pulitzer Signature Store

Pink Leopard, a Lilly Pulitzer Signature Store

Wrap-Up

Throughout the United States, there are so many excellent Lilly Pulitzer Signature Stores to support, empower, and shop at. Happy Shopping Small!!!

XOXO – Katie <3

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50+ Fall Preppy Outfits From a Lifelong Preppy

***Please note that this 50+ Fall Preppy Outfits From a Lifelong Preppy blog post will be updated and recirculated periodically. This post has most recently been updated as of July 2026.***

Believe it or not (as I’m writing this in July), Fall is just around the corner! Andddd, my fellow Preppies, it is NEVER too early for some preppy Fall outfits inspiration. Hopefully, this outfit guide gives you your own style inspiration, too.

*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 & My Preppy Outfits Archive page.

Looking for ways to save on your favorite preppy brands?!?! Check out my Poshmark, where I update the latest and greatest secondhand preppy deals every week!

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!

50+ Fall Preppy Outfits From a Lifelong Preppy

My Fall Preppy Outfits Essentials

50+ Fall Preppy Outfits

1 – A Fair Isle moment (plus my favorite stretchy pants!)

2 – Nothing says Fall than a Hill House Nap Dress!

3 – Tweed + tulle = heaven

4 – I’m so glad I scored this adorable beaded canvas tote + paired it with a fun Ruffle dress

5 – Printfresh skirts can truly be worn year-round

6 – Green seersucker for Fall?!?! I think YES!

7 – This cashmere sweater + dress combo is something I still think about

8 – A silk scarf truly adds a dressy factor to a jeans + sweater look

9 – Love me a fun block print dress for a warmer Fall day

10 – Purple ruffles is always fun for a night a the theatre

11 – Camo + Vineyard Vines for hiking in West Virginia?!?!?! OH YES!

12 – Fall florals are a favorite of mine

13 – Loved styling this Cabana Life dress with a canvas tote to brighten up Fall days

14 – A red dress + bow for Fall in Central Park

15 – I always love the versatility of Hill House Nap Dresses for Fall, especially when styled over a sweater + leggings/tights!

16 – Silk skirts + cashmere sweaters scream sheer elegance (and rooftop bar in the Fall!)

17 – Silk Scarves always add a nice, polished look to a sweater + jeans/slacks

18 – A sweater + midi skirt is also a Fall favorite

19 – The classic Fall wool skirt + Blazer combo

20 – Still gushing over these shots in my Lele Sadoughi bow!

21 – I love Fall floral moments, always, especially with a quilted jacket 🙂

22 – Mixing prints is always a vibe!

23 – Fall florals anyone?!?!?!

24 – Who doesn’t love a fun + floral Fall vest?!

25 – We also LOVE another Hill House Nap Dress

26 – A Pink plaid wrap is the BEST!

27 – A purple Lilly Pulitzer moment for the win 🙂

28 – Another fun Lilly Pulitzer moment with my go-to ankle booties!

29 – A long vest + stripes 🙂

30 – This black Mockneck dress is SOOOO elegant and perfect for Fall dinners out

31 – This Pink + plaid layered look for sightseeing in Boston is still a look I swoon over

32 – This Fair Isle cardigan is still a Fall favorite of mine

33 – I also loved this dark purple Tweed Dress for office days

34 – Pink cashmere + Burberry plaid vibes was a dream come true

35 – Who doesn’t love a vest + Emerald Green moment?!

36 – LOVE me a Pink leopard moment <3

37 – These ankle booties make every Lilly Pulitzer look perfect for Fall!

38 – I also still dream about this look when in Philadelphia!

39 – This fringe cardigan is perfect to style Lilly Pulitzer for Fall, too!

40 – Still am always pulling for this lounge set and adding on a fun wool scarf to it

41 – This ruffled rainbow dress is such a fun occasion look

42 – Anything army green + pink is always a go

43 – Gold midi skirts + lady cardigans means heaven on earth

44 – We love a good NFL fangirl moment with our Juicy Couture sweats (Raise Hail!!!!) :)))

45 – This Navy block print dress is such a Fall favorite especially with pops of pink

46 – Lounge sets dressed up with a fun blanket scarf are for the win

47 – A bright orange shift layered is so fun for Fall

48 – Tweed shifts + silk scarves are perfect for Fall

49 – We LOVE a good white for Fall moment!

50 – Still LOVE this dress and corduroy Blazer moment

51 – Always loving a work shift with a silk scarf

52 – Lilly Pulitzer + cardigans is always a Fall go

53 – Andddd, who doesn’t love a good lounge set?!?!

Wrap-Up

It is always SO MUCH FUN to look through all of my preppy Fall outfits from years’ past. I am SOOOOO excited to style many more preppy Fall outfits for the next season (and beyond!)!

XOXO – Katie <3

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Master List: The 17 Best Things To Do In Porto, Portugal (2026 Edition)

***Please note that this Master List: The 17 Best Things To Do In Porto, Portugal Travel Guide will be updated and recirculated periodically to reflect the most up-to-date information. This list was most recently updated as of July 2026.***

There are so many incredible things to do in Porto, Portugal – a smaller but mighty city in Northern Portugal known for its port wine, stunning riverside views, and magnificent tiles. This guide will walk you through the best 17 things to do in Porto, Portugal.

For more travel abroad inspiration, check out my exploring 50 Countries Expedition page.

Master List: The 17 Best Things To Do In Porto, Portugal (2026 Edition)

Where To Book

The 17 Best Things To Do In Porto, Portugal

Where To Book

Now, where do you book some of the many best things to do in Porto, Portugal?! GetYourGuide! GetYourGuide is an excellent spot to search for, reserve, and experience all of your tours and activities in any city. With GetYourGuide, you’ll have all of your tickets and reservations in one central location with easy access to add experiences to your calendar, too. Truly, GetYourGuide is a one-stop-shop for all of your travel ticket needs.

Check out GetYourGuide’s tours and activities in Porto, Portugal here.

The 17 Best Things To Do In Porto, Portugal

Igreja de São Pedro de Miragaia in Porto, Portugal

1 – Learn more about Port wine via a guided tour and tasting at Calem

Calem is one of Porto’s many Port wine wineries! I learned ALL about Port wine also known as port – a Portuguese fortified wine which is produced in Northern Portugal’s Douro Valley region – while on a guided tour of Calem. Throughout my guided tour, my group’s wonderful guide transported us to the world of developing Port wine. From the temperature-controlled rooms full of barrels producing it, to learning about port food pairings, and the heritage of what Portugal proudly calls a “spiritual drink.” At the end of the guided tour, a complimentary Port wine flight and tasting was included. Such a lovely time to end the tour! Book your guided tour at Calem here.

2 – Wander alongside the Douro River and walk across the Six Bridges

One of the best ways to savor your time in Porto is to simply enjoy the several waterfront views alongside the city’s notable Six Bridges. Visitors can also walk across several of the Six Bridges, too, via pedestrian walkways (I recommend following the people and crowds, though, for safety purposes whenever you do!). Whether it be sunrise, sunset, or midday, you will easily never get over the riverside beauty and charm that Porto has to offer!

3 – Savor a Spritz Overlooking Porto at Miradouro Ignez

A hilltop terrace bar overlooking the city as well as the Douro River. Coincidentally, I stumbled upon this lovely spot while exploring the beautiful streets of Porto near my hotel. And, Miradouro Ignez was a TOTAL surprise and dream come true of a spot to be, as I happened to show up during sunset. Indeed, a right place at the right time moment!!

4 – Create your own souvenir by painting an authentic tile through a workshop

Portugal is known for their iconic tiles nationwide. SO, why not paint an authentic tile while in Porto?! Many of these authentic tile workshops come with wine and additional drinks/snacks to enjoy while you paint and take home a souvenir to remember an incredible trip. Book your experience here.

5 – Sample Port wine via a tasting at Ramos Pinto

Founded in 1880, Ramos Pinto is one of the Douro Valley’s oldest and well-known wine producers. After walking across one of Porto’s notable Six Bridges, I found myself strolling into Ramos Pinto for a nice glass of Port wine within its tasting room. Ramos Pinto also offers tastings, too!

6 – Take a Six Bridges Douro River Cruise

An excellent way to learn more about wonderful Porto is to see the city on the river via a Six Bridges River Cruise. I opted to do a Sunday afternoon river cruise lasting approximately an hour. It was a great way to see the city in Portugal’s semi-chilly late February weather. Personally, I could not stop snapping photos on my camera and getting to know Porto from the river! Book your Six Bridges Douro River Cruise here.

7 – Admire the famous hand-painted tiles throughout the city including at São Bento Railway Station

Portugal is known nationwide for their iconic hand-painted tiles, and you can see some of these tiles up-close at the São Bento Railway Station: a 20th century terminal in the civil parish of Cedofeita, Santo Ildefonso, Sé, Miragaia, São Nicolau e Vitória. Whether or not you are traveling in and out of this railway station, it is truly worthwhile to explore and admire all the tiles at. You can *even* book a tiles walking tour to explore them and learn about their unique history in Portugal, too. Book your tiles walking tour here.

8 – Immerse yourself in the life, history, and culture of Porto via a guided walking tour

Although I didn’t add a guided walking tour on my own itinerary, I am a firm believer that doing so is one of the best things to do in Porto, Portugal (or any city for that matter!). Truly, you get to learn all about the history, life, culture, key sights, and more of a city through a walking tour. Book your guided walking tour of Porto here.

9 – Relish the architectural beauty of the beautiful bookstore of Livraria Lello

This is a Neo-Gothic architectural landmark in the heart of Porto. Livraria Lello is an iconic bookstore with an incredible history behind it. Book your visit of Livraria Lello here.

10 – Climb the 225 steps of Clérigos Tower and take in stunning skyline views

Boasting panoramic skyline views of Porto’s city center, Clerigos Tower gives visitors the opportunity to get in an excellent workout with a big reward at the end while also getting to admire the Baroque facade of the Igreja dos Clerigos and to see the Irmandade dos Clérigos Collection and the Christus Collection. Book your experience here.

11 – Wander through Porto’s very-own UNESCO World Heritage Site the Ribeira district

The Ribeira District lines the banks of the Douro River and charms visitors with its medieval alleyways, colorful buildings, and magical atmosphere around every corner. Truly, if you are planning to get lost on the streets while in Porto, the Ribeira District is the perfect place to do just that!

12 – Tour the largest wine cellar in the historic quarter of Vila Nova de Gaia and taste Port wines at Cockburn’s Lodge

With roots dating back to 1815, Cockburn’s Lodge is a higly-regarded everyday Port wine well-known for its fruit-forward and accessible style with two flagship styles: Special Reserve and Fine Ruby. Cockburn’s Lodge offers a variety of experiences, including tours and tastings. Book your experience here.

13 – Enjoy a live Fado show

Rooted in the Latin word for “destiny” or “fate,” Fado music is tied to the historical hardships that the Portguese faced over the years. It typically consists of a lone vocalist accompanied by a traditional 12-string Portuguese guitar. Book your traditional Fado show experience here.

14 – Learn how to cook local delights via a cooking class

One of the most interactive and unique ways to immerse yourself into a new city’s life and culture is to start cooking their cuisine. A cooking class is 10000% the best way to learn about the locals and do as the locals do and usually with a local, too. Book your cooking class experience here.

15 – Immerse yourself in Porto’s breathtaking Porto Cathedral with a guided tour

A Roman Catholic church in the historic city center, Porto Cathedral is one of Porto’s oldest monuments and significant local Romanesque monuments. Book your tour and visit of Porto Cathedral here.

16 – Enjoy delicious Portuguese cuisine and wine pairings at UVA By Calem

Offering a friendly atmosphere and quality hospitality while overlooking Porto, UVA By Calem focuses on curating delicious Portuguese eats with incredible wine pairings to top it all off!

17 – Get lost in the streets

One of my absolute FAVORITE things to do when I travel as previously mentioned in both my Madrid and Barcelona posts (here and here), especially when in a brand new-to-me city is to simply get lost in the streets. Luckily for you, Porto is home to some of the most brightest and colorful buildings. Some of which consist of unique tile work on its magnificent structures. Portugal showcases some of the world’s most beautiful azulejo tiles, and Porto proudly displays them throughout the city.

Wrap-Up

Indeed, Porto, Portugal is a magnificent city with so much to do and enjoy! Whether you’re savoring a glass of Port, taking in incredible tiles and architecture, getting lost in the magic of it all, or taking in some riverside views, Porto truly has it all.

XOXO – Katie <3

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Preppy Outfits Diaries – June 2026

From Summer in Italy to Americana back at home, June 2026 was definitely one of my most memorable months to date – preppy outfits and memories, alike! To kick off the month, I hopped on a Transatlantic flight to Europe to celebrate my college roommate’s wedding and spend 12 incredible days under the Tuscan sun in Tuscany, Italy. Then, I came home and started celebrating all-things America 250 as the festivities kicked off locally. Overall, I have had such a fun month and start to Summer 2026!

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Preppy Outfits Diaries – June 2026

My Favorite Pieces

Styling outfits for both Italy and America 250, there has definitely been a mix of my favorite pieces for June 2026’s preppy outfits. Whether it be my go-to travel shoes and travel tote or my go-to Summer sandals and Summer crossbody, June 2026’s preppy outfits consisted of a lot of the same accessories being styled throughout the month.

My Outfits

Here’s to styling many more fun Summer outfits in 2026!

XOXO – Katie <3

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