Have you heard of preppy style and wondered if it is a clothing style you should consider adopting for yourself?

In this post, you’ll learn all about preppy style, where it comes from, and how you can dress preppy.

You’ll find lots of examples of preppy outfits as well as the best 20 preppy women’s brands of 2024.

This post may contain affiliate links. Please see my full disclosure policy here for more information.

What clothes are considered preppy?

Preppy clothes are considered a classic, old-money style of dress.

This East-Coast ivy league and boarding school-chic style emulates the clothes worn by high society. It’s the attire one would wear to the country club, yachting, attending a polo match, while at Ivy-league school, and vacationing in Cape Cod, The Hamptons, or Palm Beach.

Although the “preppy style” originated in the 1920s, This style of dress became wildly popular in the ‘80s with the publication of The Official Preppy Handbook and later, True Prep: It’s a Whole New World, written by Lisa Birnbach.

More recently, author and illustrator, Kate Schelter brings preppy style to life on the pages of Classic Style: Hand It Down, Dress It Up, Wear It Out.

As I mentioned before, the preppy style originated with the wealthy.

But no matter your lifestyle or your budget, anyone can adopt a preppy style!

You may be wondering if preppy is still in style.

The answer is yes. ALWAYS yes.

There’s a reason for this.

Because preppy isn’t a trend. It’s actually the opposite of following trends.

Preppy is classic.

Think of it as style passed down by generations. Mother’s pearls. Daddy’s blazer with worn patches on the elbows. Or grandfather’s monogrammed cashmere sweater.

Preppy is a style that stands the test of time. So while other trends come and go, preppy will always be in style.

How do preppy people dress?

Preppy people wear classic colors including lots of navy, cream, red, and khaki. They choose classic brands and styles that can be worn again and again.

Garments such as button-down shirts, blazers, pleated skirts, shirtdresses, trenchcoats, crew-neck or v-neck sweaters, polo shirts, turtlenecks, and classic-styled trousers.

Accessories include tote-style bags, loafers, pearls, gold jewelry, silk or cashmere scarves, and classic hats.

For women, the preppy style is pretty and sophisticated but not overly sexy.

Preps like to wear top-quality brands while at the same time not wearing large logo-heavy garments.

You can check out the best preppy brands later in this post with lots of outfit ideas and links to each company.

How can I be preppy?

Start by checking out the preppy brands and outfit ideas below.
Notice the styles are classic, the logos are barely noticeable, and they aren’t following the latest trends.
Add a few items at a time to your wardrobe. Maybe start with a classic button-down shirt that you can wear with jeans, skirts, or shorts.
Invest in preppy accessories. They may be a bit more of an investment but you’ll have them and use them for years to come. Consider accessories such as tote bags, scarves, classic jewelry, preppy belts, and shoes.

20 Preppy Women’s Brands to Shop

#1. Barbour

Whether you’re planning a weekend pheasant hunting or horseback riding, Barbour is the classic outerwear brand for such events. It’s also perfect for outdoor fun such as pumpkin carving, walks in the forest, or jaunts to an apple orchard.

Barbour makes top-quality outerwear you’ll own for years to come. The jackets and vests come in classic shades and feature fabrics such as quilted nylon and water-resistant waxed cotton. Attention to detail includes coordinating plaid lining, warm pockets lined with moleskin, and lots of zippers, snaps, and vents for easy outdoor movement and comfort.

Barbour products featured above:

#2. Burberry

If you want to dress like a queen, look no further than Burberry. Granted Royal Warrants by both Queen Elizabeth II and Prince Charles, this Bond Street fashion house has been a premier British brand since 1856.

Burberry is known for its iconic trenchcoat as well as the print originally used to line the coats, the Burberry Check.

The Burberry quintessential plaid and top-quality construction have made the brand legendary. You can now wear Burberry as a full clothier including sunglasses, hats, coats, sweaters, handbags, leather goods, and scarves.

Burberry products featured above:

#3. Draper James

This sweet Southern brand is the brainchild of Legally Blondes, Reese Witherspoon.

The preppy brand is filled with pretty dresses and accessories with a Southern twist. You’ll want to fill your closet with the chambray, gingham, and magnolia printed garments that make this brand even sweeter than your mint julep.

Whether you are headed to a derby party or sipping sweet tea on the veranda, Draper James is a go-to brand for girls who want a preppy look.

Draper James products featured above:

#4. Dudley Stephens

If you’re looking for an environmentally conscience preppy brand, consider Dudley Stephens. This female-owned company sources recycled fabrics to help keep plastics out of landfills and oceans.

You’ll love this brand if you want to look like you are ready to spend the day hitting the slopes or shopping boutiques in Vail, Aspen, or Park City.

Their signature silhouette is the fleece turtleneck. It comes in a wide variety of colors and several lengths to flatter your figure.

Dudley Stephens products featured above:

#5. Hunter Boots

Keep your feet warm and dry no matter the weather in these waterproof, handcrafted, certified vegan boots from Hunter.

Another iconic brand, Hunter holds two Royal Warrants of Appointment to HM The Queen and HRH The Duke of Edinburgh.

“Wellies” are a favorite preppy wardrobe staple and come in lots of fun colors and styles. A few of our favorites are listed in the photo above including the Original Tall boot, the Short boot, and the Chelsea boot.

Hunter Boots featured above:

#6. Kate Spade

Kate Spade New York began in 1993 when Kate Brosnahan Spade couldn’t find the utilitarian bag she craved. Instead, she decided to create her own and launched the brand with 6 versions of the Sam bag.

Today, the brand features accessories including handbags, shoes, scarves, jewelry, clothes, and other everyday items with a preppy aesthetic.

Kate Spade products featured above:

#7. J. Crew

For more than 35 years, J. Crew has been outfitting prepsters with classic looks at an affordable price. Their philosophy is “they make timeless clothes that last a lifetime…and pair them with of-the-moment styles season after season.”
This allows you to create a capsule wardrobe with essential pieces and then mix in a few new items each season to keep your wardrobe fresh and fun.

J. Crew products featured above:

#8 J. McLaughlin

Founded in 1977, J. McLaughlin is a New York based fashion brand focused on creating classic, quality pieces you’ll have in your wardrobe for years to come.

Whether you are looking for clothes for work, sport, or play, this preppy brand offers pieces to suit your needs with exclusive prints and excellent craftsmanship.

You’ll find swimwear, dresses, blouses, skirts, outerwear, and sweaters. They also make preppy accessories including shoes beautiful wicker handbags, scarves, hats, belts, and sunglasses.

J. McLaughlin products featured above:

#9. Jack Rogers

Inspired by Jacqueline Kennedy Onassis, Jack Rogers makes perfect preppy footwear. The brand started with the Original Jacks, finely crafted sandals with a unique circular leather design.

Today it has branched into many variations and colors of Jacks as well as other sandal styles, espadrilles, loafers, boots, slides, heels, and wedges all with a preppy vibe.

In addition, Jack Rogers makes embroidered sandals emblazoned with lobsters, anchors, ginger jars, and of course, monograms. (PS. Preps love ANYTHING and EVERYTHING monogrammed!)

Jack Rogers shoes featured above:

#10. Kiel James Patrick

If you are looking to add some New England-inspired preppy jewelry to your wardrobe, look no further than Kiel James Patrick. All of the jewelry is designed and crafted in Rhode Island and invokes a sea-faring vibe of ropes, anchors, flags, and knots.

The brand has expanded into other accessories and clothing and remains a staple for preppies everywhere.

Kiel James Patrick products featured above:

#11. Lacoste

Steeped in tennis history, Lacoste was founded by French tennis legend, René Lacoste, a four-time international champion and the world’s best player in 1926-1927.

Due to his tenacity on the court, he got the nickname “the crocodile.” He took the name to heart and started wearing crocodiles on his blazers and shirts.

That launched a brand that is still known for its crocodile emblem and high-quality athleticwear that can be worn on and off the court.

Lacoste products featured above:

#12. Lands End

You’ll be able to fill your closet with lots of preppy basic pieces to mix and match with Lands’ End. This preppy brand got its start selling sailboat equipment to racing sailors and eventually grew into preppy apparel for all walks of life.

Not only do they design the typical preppy garments such as dresses, shirts, skirts, shorts, swimwear, outwear, they also create other must-have apparel including bras, underwear, activewear, and a large selection of women’s plus sizing.

Lands’ End products featured above:

#13. Lilly Pulitzer

Do you think a preppy wardrobe is full of plain, boring colors? Lilly Pulitzer will prove you wrong with a vibrant collection of patterns and prints that make any day a sunny one.

Back in the late 1950s, Palm Beach socialite Lilly Pulitzer started a juice stand. Since her clothes were getting stained by the juices she asked her dressmaker to create a dress that would hide the stains. The result was a cotton print shift dress in citrus colors.

The dresses quickly became more popular than the juice and a brand was born. Today Lilly is still known for unique and colorful prints and figure-flattering silhouettes for the stylish, preppy girl.

You’ll find party-ready dresses, resort wear, stand-out work clothes, and activewear for golf, tennis, and leisure.

Lilly Pulitzer products featured above:

#14. Ralph Lauren

Years ago, I saw Ralph Lauren interviewed. When he started in the fashion industry, he was Ralph Lifshitz, a New York men’s ties salesman. He said that he'd see all the wealthy New Yorkers heading to the Hamptons for the weekend to party at their seaside mansions.

He envisioned what their lives would be like - attending polo matches, gala events, yachting, and lounging. So he set off to create clothes that fit that lifestyle and forever changed retail as we know it. Lauren was the first to create not just a brand but a complete brand lifestyle including clothes, home goods, and furniture.

Ralph Lauren garments featured above:

#15. Sail to Sable

According to Sail to Sable’s founder Jennifer Stocker, the brand got its start from her original design, the tunic dress. That silhouette will forever be a part of the brand’s signature pieces.

They focus on easy-to-mix and match coordinating prints, bold colors, and stripes.

Sail to Sable garments featured above:

#16. Southern Tide

Southern Tide products featured above:

#17. Talbots

Talbots was started in 1947 by New Englanders Nancy and Rudy Talbot. Today the brand focuses on modern classic style creating versatile clothing you’ll wear again and again that suits every area of your lifestyle.

This preppy women’s brand features size-inclusive clothing to fit 0-24.

Talbots products featured above:

#18. Tory Burch

Tory Burch is an American lifestyle brand that mixes classic style with bohemian elegance and embraces the spirit of adventure with character, color, and beauty.

The collection includes ready-to-wear, shoes, handbags, accessories, watches, home, and beauty.

Tory Burch products featured above:

#19. Tuckernuck

Tuckernuck is named after a small island located just off of Nantucket, MA. It’s where the founders of the brand, three friends, spent many happy summers together.

The brand embodies their love of Nantucket and the nostalgic style represented there. They create classic yet unique garments meant to suit the lifestyles of today’s women.

Tuckernuck products featured above:

#20. Vineyard Vines

Last on the list, but by no means least, is Vineyard Vines. Started in 1998 by brothers, Shep & Ian Murray, with the desire to create a lifestyle brand with a relaxed casual style reflecting life on Martha’s Vineyard.

Today the brand sells men’s, women’s, and children’s apparel with a focus on the preppy lifestyle including fishing, golf, derby parties, and enjoying life.