15 Must-Have Modern Preppy 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 centre, 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.
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 started out 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 selvedge denim and, of course, an eclectic array of the critical preppy item, the OCBD.
Tommy Hilfger 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 definitely 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.
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.
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 fit. 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.
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 colour 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’ 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 colours 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.
Founded by Jeremy Hackett in London in 1983, Hackett was one of the original modern British tailoring pioneers, synthesising 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.
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 flavour to its own unique brand of preppy clothing.
Starting out making OCBDs and flannel shirts, GANT soon gained favour with a burgeoning middle-class audience in America who were clamouring 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 colour, pattern and technical innovation.
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.
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.
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 colour 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.
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.
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 who capitalised 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.