Explore the history behind prep as well as where to find the most iconic preppy clothing for men online from polos to chinos to Repp ties and more.
You don’t need to be an Ivy League alum to enjoy preppy men’s clothes. Find out more about the best men’s preppy clothing brands to turn to on the internet.
The History of Preppy Clothing
Preppy fashion has its roots in the traditional apparel of swanky preparatory schools and elite universities. From the start, the style has been associated with money, class, and education, and it has also brought to mind the sports enjoyed by blue-blooded people.
In the early years of the 20th century, preppy fashion signaled the status of male students in exclusive institutions. Picture young men in button-down shirts or knit sweaters. Think of rowing clubs and tennis courts on campuses with old, ivy-covered buildings.
Over time, the preppy style evolved, expanding to women’s clothes and including a greater variety of garments. Rugby shirts, for example, started getting worn off the pitch in the 1950s, and John F. Kennedy popularized the New England preppy look in the 1960s by wearing chinos, Oxford shirts, polo shirts, and blazers. In the 1980s, the preppy style continued to have aristocratic icons, particularly Princess Diana, but it also became further democratized and entrenched in mainstream fashion.
While the look has fallen in and out of fashion over the years, today, the preppy aesthetic is enjoying a bout of popularity.
“The way that the industry has presented so-called ‘preppy’ clothing in the past has been at worst problematic and at best cringeworthy and corny,” notes Rowing Blazers Founder Jack Carlson on the brand’s website. “But for me today, that vibe doesn’t ring true.” Carlson and other modern designers are on a mission to redefine how people think about preppy attire.
With its mix of informality and refinement, preppy fashion is versatile, suitable for a beach or a professional setting, especially if you want a business casual look. It maintains its elite associations, bringing to mind garden parties, sailing, and golf. But it’s also being worn in a wider variety of ways by a larger number of people.
Traditional Prep vs. Modern (New) Prep
Not all prep is the same. While the internet has carved up prep into nearly endless subcultures and aesthetics, at a very basic level, the look can be broken down into two categories: traditional prep and modern prep.
On one end of the spectrum is the Trad Prep and Ivy aesthetics, which are more formal and buttoned up, featuring pieces like blazers, repp ties, crisp chinos, and polished loafers. (Think Dead Poets Society or David Spade’s character from PCU.)
On the other end is the modern prep aesthetic, which has been referred to derisively as the frat look. Modern or new prep features more informal and often loud pieces from pink polo shirts and yellow chubbies short-shorts to lobster (or other critter) print pants and bright-blue whale ties.
In the middle, you have entire collections of preppy clothing — gingham shirts, button-down oxfords, rugby shirts, cardigans and quarter zip sweaters — that can be dressed up or down to fit a modern or traditional prep look. Companies like J. Crew and Bonobos meet men at that middle ground.
Ivy and Trad Prep: Iconic Preppy Clothing Brands
These are the most iconic brands to find Ivy and Trad Prep looks for men:
- Brooks Brothers – Founded in 1818 as a family-owned business, Brooks Brothers is the oldest clothing brand in the U.S., and its garments became a foundational part of preppy fashion. Important fashion developments originated from Brooks Brothers, including the creation of the button-down collar, and the brand boasts 40 U.S. presidents among its elite clients. The extensive selection of preppy men’s clothes includes patchwork madras windbreakers, cotton poplin chinos, tartan lounge pants, cotton-cable tennis sweaters, and striped polo shirts sporting the brand’s Golden Fleece logo.
- Ralph Lauren – After working for Brooks Brothers in the early 1960s, Ralph Lauren launched his own neckwear line and became a fashion giant. With a world-famous logo of a polo player on horseback, Ralph Lauren has exerted a profound influence on preppy attire. RL’s iconic items include mesh polos, doeskin blazers, Oxford shirts, cricket sweaters, and crew-neck sweaters that display an American flag with 13 stars and stripes. Ralph Lauren “made an updated version of Ivy and really summoned in the era of the preppy by introducing the polo shirt to the canon of Ivy clothes,“ says Avery Trufelman, host of the podcast Articles of Interest: American Ivy.
- Sid Mashburn – After working as a designer for J. Crew, Ralph Lauren, and other iconic brands, Sid Mashburn launched his Atlanta-based company in 2007 with his wife, Ann. The Sid Mashburn brand represents impeccable taste and fine craftsmanship. Among the many preppy options for men are V-neck cardigans, camp moccasins, long-sleeve polos, Oxford shirts with soft blue stripes, and woven belts made of chocolate leather.
- Bonobos – Known best for its high-quality chinos, Bonobos aims to help men find the perfect fit and build a preppy wardrobe that suits their personal tastes. Bought by Walmart in 2017, Bonobos was launched a decade earlier by Andy Dunn and Brian Spaly. Along with the chinos, other brand favorites include Henley shirts, Italian wool topcoats, Merino mock-neck sweaters, and the festive-looking Riviera short-sleeve shirts.
- J. Crew – Although it originated in the 1940s, J. Crew really took off in the 1980s, becoming a classic American brand that epitomized fun and popular preppy fashion. Although it has evolved to succeed in an age of TikTok and Instagram, J. Crew continues to offer the timeless preppy styles that made it so influential. Fine examples of menswear include jacquard ski sweaters, slim-fit stretch jeans, Donegal wool blazers, seersucker swim trunks, and Oxford shirts made with organic cotton.
- Paul Stuart – Exquisite tailoring is a key characteristic of Paul Stuart, a luxury brand that’s best known for its impeccable suits. Founded in 1938 by Ralph Ostrove, the influential brand offers outstanding preppy apparel. Examples include striped performance polos, double-breasted cardigans, cashmere turtlenecks, and lightweight wool trousers.
- Billy Reid – Based in Florence, Alabama, Billy Reid has created clothes that convey the spirit of a modern-day Southern gentleman, and his brand’s dominant values are authenticity and superior craftsmanship. Reid had to overcome major setbacks to enjoy his current success, which includes a celebrity client list. Among the preppy clothing for men are lightweight corduroy pants, moleskin jeans, pea coats made of Melton wool, long-sleeve herringbone polos, and pullovers made partly of yak yarn.
- J. Press – In 1902, Jacobi Press founded J. Press on the Yale University campus, and the brand became a bastion of traditional Ivy League menswear. One of its notable items was the three-button sack suit, and it created other garments that became hallmarks of Ivy-style fashion. Its impressive selection of preppy clothes includes striped rugby shirts, alpaca wool jackets, Oxford shirts with a flap pocket, cable-knit cardigans made of lamb’s wool, and crew-neck sweaters displaying a university logo.
- L.L. Bean – Boots and other outdoor apparel are the mainstay of L.L. Bean, a renowned Maine brand that has outfitted hunters, mountain climbers, Arctic explorers, and other people who love to be in the open air. Launched roughly a century ago by Leon Leonwood Bean, the innovative brand has also become a great resource for preppy clothes. The top picks include slim-fit flannel shirts in Scotch plaid, striped fleece pullovers, and the brand’s signature field coats, fishermen sweaters, and Bean boots, which have full-grain leather uppers.
- Lacoste – The little green crocodile is one of the most famous fashion logos in the world, adding a distinctive touch to the sportswear and other casual clothes from Lacoste, a French brand launched in the 1930s. Rene Lacoste, who founded the brand with Andre Gillier, was a star tennis player, and he helped popularize polo shirts on the court. Lacoste’s polos and button-down shirts are largely responsible for its place among the top preppy men’s clothing brands.
- Orvis – In 1856, Charles F. Orvis launched a business for fly-fishing equipment, and it later expanded into a lifestyle brand associated with outdoor adventures and high-quality apparel. Headquartered in Vermont, Orvis offers an array of preppy clothing for men, such as long-sleeve poplin shirts, quarter-zip sweaters made of Merino wool, and Sherpa fleece vests.
- Faherty – Founded in 2013, Faherty is a family-run brand with an outdoorsy and relaxed vibe and a commitment to sustainability. A favorite of Matthew McConaughey, Neil Patrick Harris, and other celebrities, the brand produces high-quality apparel that you can easily incorporate into preppy outfits. Check out some of Faherty’s best-selling menswear, including sweater shirts, marled cotton cardigans, and knit blazers.
- Barbour – The most famous item from Barbour is the waxed cotton jacket, a prime example of how this high-end British brand excels at stylish and durable outerwear. Founded in 1894 and owned by the same family to this day, Barbour has also recently collaborated with Moncler for a menswear collection that blends the iconic styles of both brands. Along with outerwear, the preppy men’s clothes from Barbour include chinos, moleskin trousers, and chukka boots.
- Armor Lux – As a French brand headquartered in Brittany, Armor Lux draws on maritime themes and the local region for inspiration. For example, it continues to make the Breton top, a garment that originated in Brittany as a fisherman’s shirt and became a part of modern-day preppy outfits. The brand, which was launched by Walter Hubacher in the 1940s, gives you a great selection of preppy men’s attire, such as wool cardigans, cotton trousers, and striped fisherman jumpers.
- J. McLaughlin – The McLaughlin brothers, Jay and Kevin, launched their sportswear brand in 1977, and it became known for classic casual clothes, excellent craftsmanship, and a commitment to supporting the communities at the brand’s retail locations. Beautiful prints are a specialty of this Brooklyn-based brand, though you’ll find plenty of preppy men’s clothes in solid colors as well. Check out the silk knit ties, cashmere sweaters, Fair Isle socks, wool blazers, and button-down shirts made with Bengal stripe fabric.
New Prep: Modern Preppy Clothing Brands
Other companies have taken prep in another direction. The brands below offer a bolder and more modern take on the preppy aesthetic.
- Boden – Founded in 1991 by Johnnie Boden, this British brand is probably known best for making posh women’s clothes, but it also has a strong selection of preppy menswear. To achieve a clean, smart look, check out Boden’s slim-leg chinos, moleskin blazers, striped rugby shirts, and cashmere half-zip sweaters.
- Rodd & Gunn – This New Zealand lifestyle brand, which has its origins in the 1940s, specializes in menswear with clean designs and an emphasis on neutral colors and earth tones. You can make your wardrobe more preppy with Rodd & Gunn’s Bermuda shorts, slim-fit Oxford shirts, goatskin suede jackets, and sweaters made of a cashmere blend.
- Vineyard Vines – A friendly pink whale is the logo for Vineyard Vines, a preppy clothing brand inspired by life on Martha’s Vineyard. Ian and Shep Murray, the brothers who founded Vineyard Vines in 1998, started out selling ties, and the current tie collection has beautiful prints, the motifs ranging from marine life to sports. Other preppy men’s clothes include linen buttoned shirts, quilted vests, leather flip-flops, and the brand’s popular Shep shirts, a sporty pullover.
- Pull&Bear – Launched in 1991 by Inditex, a multinational company that also owns Zara, Pull&Bear produces urban fashion that caters to young and trendy consumers. Claiming Palm Springs, California as its inspiration, the brand offers a range of preppy clothing for young men, including balloon-fit chinos, faux suede jackets, and swim trunks with a paisley print.
- Peter Millar – Founded in 2001, Peter Millar is primarily known for well-designed golf attire, including attractive polos with antimicrobial and moisture-wicking properties. However, the North Carolina brand helps men dress tastefully for many occasions, not just for golf. Standouts include water-resistant suede loafers, blazers made of wool and cashmere, and Fair Isle sweaters with beautiful patterns.
- Tommy Hilfiger – From iconic polos to stylish jeans, Tommy Hilfiger mastered casual clothing and became a classic American brand. Launched in 1985 by Thomas Jacob Hilfiger, the brand has a plethora of preppy men’s clothes, including varsity sweaters and slim-fit knit shirts. Tommy Hilfiger also collaborates with third-party brands and designers to create preppy garments, like the monogrammed chinos from the Anthony Ramos capsule collection.
- Onward Reserve – Authenticity and gentlemanly ruggedness define the spirit of Onward Reserve, which was founded in 2012 by TJ Callaway. The many high-quality options from this Atlanta-based menswear company include wool chinos, plaid sport coats, fleece pullovers, five-pocket stretch pants, and moisture-wicking button-down shirts.
- Southern Tide – As a preppy South Carolina brand, Southern Tide brings to mind a golf resort on Kiawah Island. Allen Stephenson, who launched Southern Tide in 2006, worked with his mom to develop the brand’s most famous item: the Skipjack polo. The many other preppy items range from lightweight blazers to striped swim trunks.
- Gant – Gant made its mark on menswear by innovating with shirt designs and becoming a top shirt-making brand, including supplying Yale University with preppy attire. Founded in 1949 by Bernard Gantmacher, Gant continues to excel at shirts while also offering other preppy men’s clothing. The choices include gingham broadcloth shirts, textured roll-neck sweaters, wool check scarves, and the Heavy Rugger line of rugby shirts.
- Marine Layer – Founded in 2009 by Mike Natenshon, Marine Layer is known best for its incredibly soft shirts and its California vibe, bringing to mind beach towns, ski resorts, and Wine Country estates. The brand also has an ethos of sustainability, which includes using recycled materials for some of its garments. Browsing the men’s clothes, you’ll find Tencel linen shirts, short-sleeve polos, Fair Isle sweaters, five-pocket corduroy pants, and the brand’s signature crew T-shirt.
- Aviator Nation – As an athleisure brand based in Venice Beach, Aviator Nation has a relaxed and youthful vibe, capturing what people love about Southern California. Founded by Paige Mycoskie in 2006, the brand is also known for its ethical labor practices, as the garments are produced in the U.S. by fairly compensated workers. To achieve a preppy look, check out the five-stripe crew sweatshirts, slim-fit dark jeans, and traveler jackets in sky plaid.
- Tuckernuck – Founded in 2012 by Jocelyn Gailliot, Madeline Grayson, and September Rinnier, Tuckernuck gets its name from a Nantucket island, and the clothes reflect a laid-back, classy life on a New England coast. Although Tuckernuck focuses on women’s attire, it does offer a high-quality selection of menswear from third-party brands, with some familiar names from this list. The possibilities include shorts and Henley shirts from Faherty, ribbon belts from Belted Cow, boat shoes from Sperry, and tartan pants from Castaway Clothing.
- Kiel James Patrick – In 2008, Kiel James Patrick and Sarah Vickers, his future wife, launched a business selling bracelets, and it expanded into preppy apparel more generally. Social media played a huge role in the success of this Rhode Island brand, which posts beautiful photos portraying an upscale New England life. Embroidered moccasins, monogrammed sweaters, cashmere joggers, and quarter-zip pullovers made of French terry cotton are among the clothes for men.
- Abercrombie & Fitch – When Abercrombie & Fitch was founded over a century ago, it catered to outdoorsmen, and it transformed across decades to become a wildly popular teen brand in the 1990s. Its current brand image appeals to people under 40 who want a preppy style and who care about social issues. Among the menswear options are varsity bomber jackets, slim jeans, patterned cardigans, sweater polos, and floral swim trunks.
- Hollister – Geared to teens and young adults, Hollister got its start in 2000 as a surf-wear brand. Although Hollister has the same name as an actual city in California, its Golden State origin story is mythical, as it was launched in Ohio by Abercrombie & Fitch. The brand’s best preppy men’s clothes include shirt jackets, color-block polos, muscle-fit buttoned shirts, and skinny chinos.
- Rowing Blazers – The founder of Rowing Blazers, Jack Carlson, used to compete at the World Rowing Championships, and his brand is inspired by the aesthetics of rowing clubs and Oxford University, where he attended graduate school. Since its founding in 2017, Rowing Blazers has been favored by various celebrities, such as Pete Davidson, Rick Ross, and David Byrne. The men’s attire includes colorful cable-knit sweaters and a variety of hand-tailored blazers and jackets, with designs ranging from herringbone to patchwork tweed.
- Pacsun – A Gen Z favorite, Pacsun sells in-house streetwear and sportswear and curated picks from other popular brands, such as Guess and Adidas. The Southern California company, which launched in 1980, can add some preppiness to your wardrobe with paisley-patterned swim trunks, white slip-on shoes, short-sleeve buttoned shirts with print art, and long-sleeve T-shirts with an embroidered logo.
- Tommy Bahama – Although the Tommy Bahama brand has its origins in Minnesota, it beautifully captures the spirit of beach vacations and upscale island living. The preppy men’s clothing includes moisture-wicking polos, leather slip-on sneakers, and button-down linen shirts in solid colors or eye-catching patterns. The brand’s 10-inch shorts also come in different materials and designs, like polyester shorts with a Hollywood waistband and shorts with a herringbone fabric made mostly of silk.
- Urban Outfitters – Through this Philadelphia-based lifestyle brand, you can find a mix of preppy, bohemian, and vintage clothes. Founded decades ago, Urban Outfitters has made some commitments to sustainability, including the use of repurposed items and recycled materials. As you browse through in-house labels and third-party brands, the preppy menswear that jumps out at you may include white vintage Reebok sneakers, polos and rugby sweaters from Ralph Lauren, and twill beach pants from Urban Outfitters itself.
- Castaway Clothing – Coastal life is the dominant aesthetic of Castaway Clothing, which was founded in 2005 by a pair of brothers who previously worked at their family’s iconic Nantucket clothing store. If you want to dress like you’re headed for a Nantucket beach party or boating trip, explore Castaway Clothing’s popular collection of embroidered shorts, and check out the many other options for men’s preppy clothing, such as crew-neck sweaters, rugby shirts, and corduroy pants.
- B. Draddy – Golf attire and casual menswear from B. Draddy, such as the signature Russ crew-neck sweatshirt, consistently earn strong reviews. Billy Draddy aims for his brand to embody brotherhood and superlative quality, and there are plenty of items for preppy outfits. These range from twill shorts to full-zip sweaters made of baby alpaca yarn.
- Fairway & Greene – The gentlemanly golf attire from Fairway & Greene works well for a golf course, a country club, and other settings that call for preppy outfits. This premium brand, which was founded in 1995 by Rick Martin, already offers polos and pullovers designed for the 2023 U.S. Open. Other highlights include vests made of Baruffa Italian Merino wool.
- Petite Plume – Specializing in luxury sleepwear, Petite Plume is known best for its classy pajama sets, which range in design from striped silk to bold plaid. Founded in 2015 by Emily Hikade, who used to work undercover for the CIA, the brand has become popular among British royals and other celebrities. Along with pajama sets, you can pick other items for lounging in style, such as velvet loafers, a houndstooth robe, and a V-neck top made of Peruvian Pima cotton.
- Fair Harbor – A pair of siblings, Jake and Caroline Danehy, founded Fair Harbor in 2014 with a desire to clean up the ocean. The brand uses recycled plastic bottles to make its signature swimwear. Men can buy swim trunks in solid colors or in vibrant patterns, such as banana leaves, and they also have their pick of other preppy garments, including polos, vintage-style crew-neck sweatshirts, and snug fleece outerwear with a breathable lining.
- Smathers & Branson – Peter Smathers and Austin Branson are purveyors of beautifully stitched apparel, particularly needlepoint belts and shoes. Founded in 2004, Smathers & Branson allows you to choose belts from a variety of themed designs, such as golf or dogs, and you can even develop a custom belt. As for shoes, the selection includes Belgian loafers with nautical flags and driving shoes with college colors.
- Holebrook – Preppy sweaters with windproof lining are the most distinctive item from Holebrook, a Swedish brand that specializes in high-end outerwear. Holebrook, which was founded decades ago by Tina and Peter Karstorp, makes all of its clothing in Europe. Other items worth checking out include color-block crew-neck sweaters and collarless buttoned shirts.
- Jordan Lash Charleston – Along with establishing a brick-and-mortar store in Charleston, South Carolina, Jordan Lash Charleston has an excellent online store with many preppy clothing brands for men, including several that feature on this list. Founded by the Lash brothers, Jordan and Daniel, the company produces its own clothes as well, such as sport coats and leather driver loafers. Third-party garments include knit shirts from Emmanuel Berg and floral Oxford shirts from Stenstroms.
Which Preppy Men’s Clothing Brands Do You Love?
Share your thoughts about your preferred brands, and mention any that aren’t on this list. Also, whether it’s a blazer or a boat shoe, which type of preppy apparel do you love best?
About JakeJake is passionate about exploring entrepreneurs' global journeys. He founded Modern Fellows in 2012 to get to know the entrepreneurs behind the innovative brands helping men dress sharp in the digital age. Jake has written about entrepreneurship, international business and/or fashion for outlets including Business Week, Forbes, Inc., Details Style Syndicate and Primer Magazine, and has provided analysis on international business for BBC Radio, NBC News, CNN and Time Magazine.
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