12 Preppy Clothing Brands to Shop for Classic Style

Image via Draper James

Knowing the best preppy clothing brands is a must for anyone looking for a clean cut, polished, and cheerful wardrobe. Preppy clothes are generally rooted in classic style, and have a sense of Americana about them, too.

Many of the top preppy clothing brands have actually been around for decades (or more), though there are also some relatively recent newcomers that have grown in popularity.

Here’s a list of all of the top preppy clothing labels to shop if you love the country club look.

Preppy Clothing Brands We Love

1. Lily Pulitzer

All images via respective brand

Palm Beach socialite Lilly Pulitzer made fashion history in 1959 when she created her own company, specializing in distinctive shift dresses that are both elegant and casual. Lilly Pulitzer dresses made a splash with their unique patterns, known for practicality with a spill-proof and cotton-lined design.

To this day, the name Lilly Pulitzer is synonymous with resort-wear everywhere, and is especially beloved by twenty-something, fashion-forward women who love to let loose and live colorfully. Trendy Lilly Pulitzer shift dresses average at about $150, and they make a budget-friendly statement you won’t want to miss. If you’re in the market for women’s fashion that fits a preppy and bright lifestyle, you’re looking for Lilly Pulitzer.

2. Ralph Lauren

Founded in 1967, American brand Ralph Lauren soon escalated from neckwear to menswear to today’s status as one of the top preppy clothing brands in the world. Ralph Lauren’s classic designs hail to English aristocracy and signify class, attracting high-end shoppers and eager fashionistas like. Polo shirts, blazers, and striped sets are Ralph Lauren’s niche — effortlessly cool and timeless, appealing to the modern man and woman just as much as to youth looking to fit in (or stand out).

This multi-generational, modern American aesthetic is what makes Ralph Lauren such a successful brand, with simple, repeatable designs that never go out of style. Prices are far from fast-fashion but cheaper than luxury, making Ralph Lauren the perfect poster child for an old money, happy medium, greatly beloved fashion retailer.

3. Draper James

preppy clothing bands - plaid dress

Launched by award-winning actress Reese Witherspoon in 2015, Draper James brings contemporary Southern styles to the modern American woman. Reese Witherspoon named and modeled the brand after her grandparents, digging into her Southern roots for inspiration. Feminine charm and gingham dresses are at the heart of Draper James, as well as fundamental homestyle values, making for a brand that looks good and feels good.

Timeless accessories and apparel designs are perfect for dressing up or dressing down, in styles you’ll want to rewear. Pieces average at about $100, making Draper James an affordable and alluring go-to shop you’ll want to wear everywhere.

4. Tory Burch

preppy clothing brands tory burch black and white outfit set

If you’re looking for timeless fashion pieces paired with bright travel-inspired designs, look no further than Tory Burch. Based in Manhattan since its founding in 2004, Tory Burch is a mid-luxury preppy clothing brand with women empowerment at its core. Simple ballet flats and luxe handbags are two of the brand’s most recognizable and well-loved pieces — statement accessories ranging from $200-$600 depending on style, size and seasonality.

In addition to high-end fashion, this beloved retailer also provides women entrepreneurs with business opportunities and loans through the community-based Tory Burch Foundation. For women who want to look good while empowering others, Tory Burch is a must-stop shopping destination, with unique designs and feel-good styles that make luxury worth the price tag.

5. Vineyard Vines

preppy outfit from vineyard vines

Founded in 1998 in Martha’s Vineyard, a popular seasonal vacation destination, Vineyard Vines bring preppiness to the people with a recognizable pink whale and a plethora of collared shirts. Getting their start as a tie company, and later adding clothing collections for men, women and children, Vineyard Vines styles are the quintessential New England-esque clothing stop.

With designs more commonplace than luxury, Vineyard Vines appeal to the everyday citizen who find themselves intimidated by high-end fashion but still want to make a statement in how they dress. Vineyard Vines most popular styles usually land in the $100 range, making them affordable without being cheap, and preppy without being designer.

6. J.Crew

J. Crew is an iconic American brand known for it’s timeless style. Founded in 1947 in New York City, J. Crew originally targeted upper-middle-class women seeking a sleek and mature look. J. Crew’s target audience has ebbed and flowed many times since then, sometimes struggling to keep up with the trends, yet remains relevant to this day by staying true to timeless preppy styles and quality pieces.

J. Crew sells clothing and lifestyle collections for men, women and children, often at discounted prices, giving them multigenerational appeal as high-end clothing that’s affordable, too.

7. Dudley Stephens

Dudley Stephens is a mother-daughter owned preppy clothing brand brand, founded in Greenwich, CT in 2015 with functional fashion at its heart. Known for their elevated fleecewear, Dudley Stephens’ top-selling items include monochromatic turtlenecks, tunics, and maxi dresses.

A brand known for comfort as well as status, Dudley Stephens pieces are made to be worn. Sustainability is one of the brand’s core values, using recycled fabrics at every possible turn, and constantly exploring new eco-friendly production options. Collections at Dudley Stephens range from outerwear to loungewear to bright swing dresses — a splash of color sure to brighten anyone’s wardrobe (and day)!

8. J McLaughlin

Producing classic American fashion since 1977, J. McLaughlin is a brand known for elevated styles in menswear and womenswear. Each brick-and-mortar location of J. McLaughlin is built with an entirely unique design, made to fit the architecture and aesthetic of each individual town. From individual shopfronts to their fun, casual apparel, J. McLaughlin makes quality clothes for a day (or night) on the town.

Dresses with pockets, coastal print trousers and colorful accessories bridge the gap between casual daywear and preppy socialite designs, solidifying J. McLaughlin’s place as a brand with multi-purpose and multi-generational appeal. If you’re looking for timeless fashion with a trendy twist, pop by J. McLaughlin and put traditional American styles back on the shelf.

9. Tuckernuck

Tuckernuck is one of the ultimate preppy clothing retailers, and while the store sells clothes from a variety of brands, its in-house label is perfectly preppy. If you’re looking for stripes, gingham, and pastels, head to Tuckernuck. Tuckernuck is named after a small island off of Nantucket and, you guessed it, it’s a high-end store with a preppy spin.

They offer both men’s and womens’ clothing, shoes, and accessories, and carry clothing from both their own in-house brand, as well as a range of smaller contemporary retailers. Popular brands you’ll find on the site include Pomander Place, Emerson Fry, and Faherty.

Price points range from mid-range (Think $85 for a top) to high-end (i.e. $800 evening gowns). Based out of Washington D.C., and founded by three working moms looking to create classic yet unique pieces, Tuckernuck is an online boutique and lifestyle shop with personality and high-end flair.

Named after a small island in Nantucket, Tuckernuck’s aesthetic is fitting to its namesake with New England pinstripes and classic minimalistic designs. With collections for men and women, and classic lifestyle pieces with a bourgeois twist, Tuckernuck is an ideal shopping destination for the working woman — from nights out, to the office, to your own family vacations to Nantucket.

10. Abercrombie

Abercrombie is a popular multinational fashion retailer specializing in casualwear, with a focus on designing upper scale fashion for a younger generation. Originally founded in 1892 in New York City as a seller of elite sporting goods, Abercrombie slowly transitioned into its fashion presence today as a young adult apparel retailer, without losing its high-end image.

Abercrombie introduced the trademark “casual luxury” to the fashion world, marketing to a higher class while still offering styles that appealed to a diverse range of individuals and their fashion interests. To stay relevant, Abercrombie have lowered prices and began producing trendier items, helping them appeal to a younger crowd with every quickly shifting fashion trend. From comfortable men’s and women’s clothing to timeless accessories, Abercrombie is a dream fashion destination for those seeking quality and comfort all in one.

11. Barbour

Recognizable for their waxed cotton jackets, Barbour is a luxury brand that specializes in countrywear for men, women and children. Barbour had its start in 1894 in the U.K., and now has a nationwide retail presence, while still remaining true to its roots in timeless British fashion pieces. Barbour creates what they call “lifestyle clothing”, essentially, clothing that is intended to be cherished and worn more than once. Their iconic waxed cotton jackets average at around $400, and they sell many more quality pieces, such as boots and leather gloves, to pair with this look for around $200 each. Barbour is a dream shopping destination for anyone looking to invest in quality clothing that stands apart from today’s trending patterns and fast-fashion lookbooks.

12. Hill House Home

Last but not least, there’s Hill House Home. The brand became extra popular in 2020 for its viral “nap dress,” soft, flowing dresses in pretty colors and prints that are so comfortable they could double as PJs. However, they also sell a range of preppy clothing for women, including tops, jackets, swimwear, shorts, and

What is Classic Preppy Style?

Classic preppy style revolved around timeless, polished clothing choices. The classic prep look is tailored with an element of Americana, and bit of a sportiness. Think Ralph Lauren, Tommy Hilfiger, and Vineyard Vines. They all conjure images of beachside fires, ski days, or afternoons on the polo field.

Classic prep also incorporates certain fabrics, silhouettes, and colors, too.

Seersucker suits and cableknit sweaters are classic examples of preppy staples, as are A-line dresses, simple loafers, and tailored blazers.