30 Must-Have Modern Preppy Clothing Brands For Men
From the Ivy League halls to Tyler the Creator, collegiate style has been an ever-present menswear genre. If you want to inject some preppiness into your wardrobe, these are the brands to nerd out on.
You could say that preppy style is having a bit of a moment, what with the likes of Tyler the Creator and Alessandro Michele at Gucci bringing it front and center, but in all honesty, preppy style has never gone away. From its origins in British public schools to its Ivy League adoption in the 1950s, preppy menswear laid down some deep roots.
You can understand why it has been an ever-present part of men’s fashion: youthful collegiate silhouettes meet great fabrics and even greater relaxed tailoring, then throw some sporting motifs in there and you have the perfect amalgam of smart casual Americana that’s easy to wear and a breeze to style.
We’ve curated a who’s-who of the very best brands creating that preppy aesthetic today. The look has certainly evolved over the decades, with a modern sportswear influence mixing shoulders with old-school tailoring, but it’s that amalgam that makes the modern preppy look so fun and appealing.
Ralph Lauren
Undoubtedly the grandfather of modern preppy style, Ralph Lauren is unparalleled when it comes to the Ivy League look. From the launch of Polo Ralph Lauren in 1968, when he was working out of a tiny room in the Empire State Building and doing the deliveries himself, Lauren has seamlessly combined collegiate style and the country club vibe, all wrapped up in a wholesome bag of American luxury.
All the key preppy icons are there season after season: shawl-collared cardigans, Oxford cloth button-downs (OCDBs), sports coats, herringbone blazers and chore jackets, with some technical rowing-inspired outerwear thrown in for good measure.
If there was somewhere you needed to start on your journey to prepdom, it’s at RL Towers.
Drake’s
Drake’s started life in 1977 as a haberdashery but quickly graduated to a well-respected British tailoring brand. Now it’s an almost cult purveyor of quirky-classic preppy style that combines its excellent fabric heritage with an innate ability to style its collections for the modern man who hates the traditional suit and tie.
Drake’s ‘perennials’ collection is a brilliantly curated trove of must-have pieces to build a preppy wardrobe around, such as the five-pocket chore jacket, boucle wool fleece, lambswool turtleneck, shawl-collared cardigan and a number of stunning seasonal suits.
Drake’s also does a fine line in heavyweight Japanese selvage denim and, of course, an eclectic array of the critical preppy item, the OCBD.
Tommy Hilfiger
Tommy Hilfiger has been a stalwart of modern Americana since the late 80s, leaning on the athletic collegiate side of the menswear genre rather than the tailoring aspect.
Hence, Hilfiger’s signature look is very much about comfort and leisure, combining plenty of preppy sweatshirts, hoodies and track pants with technical outerwear and denim.
It’s a more contemporary interpretation of American style than, say, Ralph Lauren, so you’ll find plenty of crew-neck sweats to pair with more traditional preppy silhouettes such as the varsity bomber.
J.Crew
For over 35 years J.Crew has produced a fine line in snappy youthful preppiness, incorporating a bright bold palette and a great array of diverse fabrics along the way.
Particularly of note is the Californian brand’s cashmere shop, which features a vast range of jumpers, knitted polos and cardigans that would easily slot into any preppy wardrobe worthy of the name, as well as the seemingly endless chino options.
But J.Crew’s true calling card is the Ludlow suit, an unstructured seasonal two-piece that comes in a variety of cloths and two cuts (slim and classic). It’s everything that relaxed tailoring should be.
Todd Snyder
As far as quintessentially American fashion pedigree goes, Todd Snyder has bundles of it. Before founding his eponymous label in 2011, Snyder held leading roles at Polo Ralph Lauren, The Gap and J.Crew, so his preppy menswear credentials are bona fide.
There’s a lot to like about Snyder’s aesthetic, not least his denim and chambray shirts, which add nice texture to a preppy outfit. Snyder also has an extensive range of chinos, jeans and sweatpants, plus a great cashmere collection, all of which are essential preppy fodder for crafting casual weekend looks.
Aimé Leon Dore
The brainchild of Queens native Teddy Santis, Aimé Leon Dore has become one of New York’s hottest labels, carving out its own unique brand of modern streetwear, Big Apple nostalgia and contemporary vision of the preppy tradition. It’s a heady mix that has gone down a storm with an evolving generation of streetwear aficionados.
ALD playfully combines elements of sportswear (basketball especially) and vintage-inspired knits with relaxed tailoring, classic preppy shirts and bold outerwear, with a brilliant collaboration with Drake’s in 2021.
Santis likes to keep the brand marketing aloof so make sure you sign up to its newsletter because the limited drops sell out real fast.
Noah NY
In Noah NY, founders Brendon Babenzien and Estelle Bailey-Babenzien have combined their love of skate, surf and music cultures with a unique take on contemporary menswear, resulting in a modern urban redux of preppy style.
Noah’s forte is in producing iconic preppy pieces such as rugby pullovers, hoodies and cardigans, alongside workwear staples such as jeans and pleated pants.
Using a bold color palette and an abundance of strong patterns, stripes and checks, the collections are really easy and fun to style with more tailored pieces such as sports coats and blazers.
Rowing Blazers
Rowing Blazers’ preppy credentials are in the name. Founded by Dr. Jack Carlson – an Oxford-educated archaeologist, former member of the U.S. national rowing team and World Championships bronze medallist – the brand is primarily known for its tongue-in-cheek interpretation of classic preppy style, using bold colors and patterns throughout its excellent blazers, rugby shirts, sweaters and polos.
Much of Rowing Blazer’s aesthetic leans on nostalgic collegiate style, but dialled up to 11. So think pink corduroy blazers, panel-blocked cardigans, ear-splittingly loud Madras check OCBDs and such like.
It’s a confident and fun interpretation of modern preppy style that never fails to put a smile on your face.
Hackett
Founded by Jeremy Hackett in London in 1983, Hackett was one of the original modern British tailoring pioneers, synthesizing the bespoke suits of Savile Row into a more wearable (and affordable) part of menswear. From there, Hackett evolved, incorporating a very English concept of preppiness with elevated classics cut from the finest fabrics.
Alongside the exemplary tailoring, Hackett also created a superb range of contemporary smart casual pieces including polo shirts, sweatshirts and gilets, in response to how the modern man’s work uniform was changing.
Today, it’s still the go-to label for understated classics it ever was.
GANT
Given that it was founded in New Haven on the US east coast in 1949, you won’t be surprised to learn that American giant GANT brings a decidedly nautical flavor to its own unique brand of preppy clothing.
Starting out making OCBDs and flannel shirts, GANT soon gained favor with a burgeoning middle-class audience in America who were clamoring for the Ivy League style. In fact, a 1954 issue of LIFE magazine declared New Haven the home of the Ivy League look (it helped that Yale was on their doorstep).
Today, GANT continues to evolve the preppy aesthetic with a modern maritime look rich in color, pattern and technical innovation.
Brooks Brothers
America’s oldest apparel brand in continuous operation, Brooks Brothers is sartorial royalty, with former GANT man Michael Bastian now Creative Director.
A fixture in New York since 1818, Brooks Brothers still carries the same seal of high-quality craftsmanship despite running into financial difficulties. All that did was streamline the brand, offering a more accessible and wearable collection of preppy staples, exemplified by Brooks Brothers’ excellent OCBD collection.
While the suits still err on the business side, the sports coats, knits and jerseys offer great value for money.
Alex Mill
Cofounded by Alexander Drexler and Somsack Sikhounmuong, Alex Mill is a brand with pedigree. Alexander is the son of Millard ‘Mickey’ Drexler – the former CEO of Gap and J.Crew, as well as the founder of Old Navy and Madewell – while Somsack was previously design director at J.Crew and Madewell. So, it’s safe to assume they know a thing or two about creating classic preppy clothing.
Taking a slower, more sustainable approach than the aforementioned companies, Alex Mill was founded on the principle that men don’t need new clothes, but rather the right clothes. The duo originally set out to create the perfect shirt, which many would say they succeeded, and have since expanded the range to incorporate all the key elements of a capsule wardrobe.
Therefore, expect all the usual preppy fare – including OCBDs, chinos, unstructured sports jackets, polo shirts and sweaters – all crafted using the highest quality fabrics and designed to be completely timeless.
Abercrombie and Fitch
Fashion is a fickle business. After dominating noughties campus style, Abercrombie and Fitch entered a period where its rep was tarnished both by corporate scandals and corny designs. Now it’s back, doing what it does best: a modern take on the Ivy look with more sweats and fewer topless models.
Hoodies, sweatshirts and joggers are some of the best buys, but also check out the brand’s Oxford shirts and jackets. The collection is rounded out by more modern wardrobe pieces like puffer coats and overshirts, but Abercrombie’s preppy roots are still there for all to see.
Golf le Fleur
Hip-hop has a long tradition of subverting the preppy look and nudging it into interesting new territory. This is Tyler The Creator’s take. The musician’s own style has long mixed skatewear and preppy fashion, and Golf Le Fleur is his luxury tribute to the latter.
Think on-point tennis shirts, wool varsity jackets and pleated pants, but all rendered in a Wes Anderson-friendly palette of pastels and earthy tones.
Lacoste
Created by French tennis whizz Rene Lacoste in the 1930s, Lacoste does more than carry its founder’s name. The brand’s famous logo comes from the fact that Rene was known as ‘The Crocodile’ on court. Nearly a century later, it’s still one of the most recognizable logos in fashion.
Best known for its iconic polo shirt, which came straight from the tennis court, Lacoste has a closet full of other preppy staples. Its vintage-style cable-knit sweaters and cardigans are particularly good, but also check out its sweatshirts, zip-up track tops and button-down shirts.
J Press
Self-described as the definitive Ivy League label, J press backs up the claim with over a century of history as a classic American outfitter. It was doing Ivy League style before Ivy League students knew they were creating a look that would last decades.
The label even lays claim to the concept of wearing tailored separates, after it bought surplus stock from England in anticipation of the Second World War. With scarcity a factor, people began wearing the brand’s mismatched blazers and trousers and making it look good.
Today, J Press is a proud heritage brand. For sweatshirts, rugby shirts, button-downs and blazers with impeccable Ivy credentials, look no further. And if your smart wardrobe leans preppy, the brand’s tailoring is pretty special, too.
Fred Perry
Another label born on the tennis court, Fred Perry has a more British sensibility, as you’d expect from the Englishman who gave the label its name. Adopted by subcultures like mods and skinheads over the decades, Fred Perry’s preppy roots are now infused with streetwear influences, too.
So, yes, there’s the famous polo shirt, but the label is also a reliable source of excellent patterned knitwear, tracksuit tops and accessories. Don’t miss its iconic barrel bag, which does office-to-gym better than most other designs.
LL Bean
Preppy clothing is sometimes mistakenly thought to start and end with campus clothing, like smart-casual college uniforms and sports-field classics that have made it to the mainstream. In fact, preppy is a broader church than that and it includes numerous aspects of all-American style and culture. Few brands are as all-American as LL Bean.
Founded in Maine in 1912, it’s a label created for the outdoors so its brand of Americana is campsite chic. Where the collection best intersects with preppy uniforms is in its practical layers. Think chunky fisherman knits, classic sweatshirts, retro fleeces and quarter-zips top.
Beams Plus
Ametora is a Japanese word derived from ‘American’ and ‘tradition’, and it’s used to describe the wave of Japanese fashion labels that took inspiration from mid-century preppy fashion – then bettered it. Among those, Beams Plus is one of the best known, and for good reason.
Paying homage to vintage Americana, but bringing a Japanese edge to its collections, Beams is casual and rugged but elevated at the same time. Striped tops, wide-leg slacks and knitted polos are among the brand’s staple styles.
Vineyard Vines
Founded on the moneyed island of Martha’s Vineyard in New England, Vineyard Vines is a preppy label born in the heart of preppy America. If you want chinos, an Oxford button-down and a quarter-zip knit to wear over the top, you won’t go far wrong here.
It’s not a boundary-pushing brand, but one that’s completely content in preppy style designed for the good life.
Crew Clothing Company
A British take on classic American preppy labels, Crew Clothing is inspired by coastal lifestyles, mixing practical pieces with smart casual staples. One side of the brand is dedicated to weatherproof outerwear and insulating layers, the other is about herringbone blazers, Oxford shirts and cable-knit sweaters.
One of the most affordable preppy labels you’ll find, it’s also a good place to stock up on polos, rugby shirts and chinos.
Billy Reid
Described by the designer himself as ‘Ivy South’, Billy Reid’s eponymous brand injects some good ol’ southern character into the classic preppy wardrobe. Based in Alabama, the label takes local inspiration in its collections.
It’s a rural, western-tinged approach to preppy. Think cowboy details in the shirts and dusty suede ranch jackets in place of traditional blazers.
He’s not necessarily a household name, but Billy Reid is one of the most decorated American designers. So expect craft, excellent fabrics and unexpected detailing in everything the label produces.
Sid Mashburn
Sid Mashburn was J Crew’s first menswear designer and went on to work for Ralph Lauren, Tommy Hilfiger and Land’s End. In other words, the man has a second-to-none CV in preppy design. He finally set up his own label with his wife Ann in 2007 and it’s a love letter to Ivy style.
From checked blazers and Madras shirts to five-pocket pants and polos, everything is utterly faithful to the preppy bible. Like a lot of brands in this genre, there’s also an outdoor edge, with hunter’s jackets and practical materials across the board.
Kamakura Shirts
One of the many Japanese clothiers who took American Ivy League dressing and bettered it, Kamakura Shirts is all about the, well, shirts. Its (almost) singular focus is to create the best dress shirts and longest-lasting casual shirts in the world.
If you’re nerdy about the style, the label produces a hefty number of Oxford shirts in various colors, patterns and fits. It also recreates iconic pieces from the past, such as shirts worn by Ivy legends like Miles Davis.
John Simons
If you’re in London and you want to know about Ivy League style, John Simons is the man to speak to. He opened the Ivy Shop in 1964 and his eponymous store has been a fixture of Marylebone for more than a decade.
The own-brand stuff is excellent: Ivy-faithful blazers in a range of styles, plus quintessential Oxford button-downs, chinos, overcoats and Madras shirts. But it’s also a place to discover and explore specialist preppy labels that Simons loves and stocks.
Warehouse & Co
If you admire Japanese labels’ insane attention to detail, you’ll love Warehouse & Co. The Osaka brand made it its mission to faithfully reproduce vintage garments that you can’t get your hands on any more and the research that goes into each piece is incredible.
For preppy fans, the label is a hotbed of mid-century American design, but made today to extremely high standards. As well as campus classics like sweats and baseball tops, it’s a great place to find 50s- and 60s-style denim.
Adsum
Founded in Brooklyn in 2015, Adsum NYC is inspired by the cities and countryside of the American Northeast. This translates to a range of clothing that mixes technical outerwear, relaxed sportswear and classic Ivy League staples, with more than a little streetwear feel to it.
Although the designs are primarily stripped back, the color palette is decidedly preppy, with bold primaries, dusty pastels and rich autumnal bringing a contemporary feel to its garments.
Most of its wares are made in Canada, so you can be assured of fabric and build quality.
GH Bass
We couldn’t pull together a list of the best preppy brands without including GH Bass, the Maine-based company founded in 1876, and creator of the stereotypical preppy shoe: the Bass Weejun.
These penny loafers have been squeaking down campus corridors for the best part of half a century and continue to be the preppy footwear of choice, perfect worn with turned-up denim or a cropped chino.
Whether you go sockless is up to you, but just know that the Bass Weejun is preppy accreditation, wherever you go.
Sperry
Given the Ivy League’s proximity to the US East Coast, the collegiate style that swept the world in the 50s was always going to be influenced by nautical references – hence the windbreakers, gilets, and maritime stripes.
One brand that capitalized on the trend was Sperry, maker of the world’s first boat shoe. If you weren’t in Weejuns then you were wearing rubber-soled Sperrys, and to this day the brand – founded in 1935 by sailor, inventor and intrepid explorer Paul A. Sperry – has stayed true to the original design and philosophy.
Now available in myriad styles, its authentic boat shoe is much imitated but never bettered. Perfect with tailored shorts, chinos, jeans and even track pants, the deck shoe is an integral part of the off-duty collegiate look.
