Preppy style may not have ever fully left—we’d argue it’s one of the few truly evergreen menswear aesthetics, and one that almost every guy has dipped a (loafer-clad) toe into at some point—but it’s certainly back right now, and in a bigger way than it’s been in years.
For the eagle-eyed prepwatchers, there were early clues that something was brewing. Brendon Babenzien’s arrival at J.Crew from Noah four years ago—and the immediate success of his “Giant Chino”—as well as the runaway success of other brands offering a modernised take on the campus look, from Drake’s to Aime Leon Dore, showed that even as guy’s fits were getting more relaxed, the staples of preppy style could easily grow with them.
The crescendo came this summer. At the Paris menswear shows in June, the Ivy League look was the only thing anyone could talk about, thanks to the one-two punch of prep-heavy styling in the debut collections from both Jonathan Anderson at Dior and Michael Rider at Celine. Then at New York fashion week in September, everybody wanted to be a preppie. The takeaway? It’s high time we took stock of the fundamentals of the preppy look.
On that subject, good news! Done right, preppy style is universally flattering, built as it is on well-styled, simple separates instead of trickier ‘fashion’ pieces. It’s also incredibly versatile: After all, these are looks that were initially designed to be formal enough for class, but still loose enough for kicking back on the quad. And while it’s classic, it’s not conservative. In fact, it provides a foundation from which to bring in more playful elements: brighter colors, bold stripes, and a certain jauntiness in how it’s all put together. Today, it’s also the secret sauce behind the charming-yet-classic styling of a long, diverse list of leading men, from Josh O’Connor to Bad Bunny and ASAPs Rocky and Nast.
Finding your way into preppy styling is about understanding its constituent parts. While so much of the look is about how pieces are combined and worn together, it also depends on a certain attention to detail: the width of a pant, the texture of a tie, or the shape of a shoe makes all the difference between authentically dapper and corny pastiche. Thankfully, that’s where we come in. Read on for our 13 key elements of preppy style, and the best places to stock up on ‘em right now.
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Oxford Shirts
Shirting is a pretty foundational layer of the preppy look, but with a caveat: what you’re looking for is a thicker, more textured fabric in a basket-weave Oxford style, which lends the whole thing a more relaxed, less ‘waiting for a suit jacket’ vibe. A button-down collar will help in this regard, too. From there, you can build out as you see fit: half of the fun of preppy dressing today is layering the rest of this list on top of your shirt. But you can’t build the house before you’ve laid the foundation.
Tweedy Blazers
The right blazer is pretty much integral to a preppier style of dressing: that mix of formal and relaxed is what the look is all about. With that in mind, the right blazer doesn’t need to be too slick, and certainly shouldn’t be too fitted: look for unstructured shapes, rounded shoulders, and masculine fabrics like tweed, corduroy, or heavy cotton, as well as sportier details like notched lapels or patch pockets. From there, it’s all about slotting it into otherwise casual looks: with jeans and a rugby shirt, or worn over a denim shirt, or used to smarten up a t-shirt, tucked into pleated pants.
Repp Ties
If we’re going to get persnickety about it, a repp tie is one that’s woven to a specific ribbed texture. But what we’re talking about here is one with a diagonally striped pattern, of the kind that became synonymous with the style of British and Ivy League schools. These ties’ slightly stuffy backstory makes them ripe for mussing up: at that much-lauded Dior show in June, repp ties were worn half-tied over one collar. And while that might look a little dopey in real life, you should still take a similarly relaxed approach. Don’t panic about achieving the perfect Windsor knot, and don’t feel obligated to colour-match with your shirt, jacket, or shoes: a curveball colour combination looks much cooler, anyway.
Chinos
“Chinos,” you’re thinking. “Sure. I’ve got those”. But the preppy look doesn’t really hold together when it’s worn with very slim-cut styles, which tend to read as more European – especially the ultra-tight, buckling-thigh-seam styles beloved of certain gym bros (which, frankly, shouldn’t be worn by anyone). Instead, look out for a fuller, roomier pair in a straight or wideish leg, made from a cotton twill which will hold its shape and break in comfortably.
Loafers
If you missed the swing towards loafers over the last couple of years, it’s not too late. In fact, your timing might be better than ever: every menswear brand worth its salt has a good pair on the market right now. If you’re looking to lean into a preppier look, opt for classic penny or tassel styles, with a more rounded toe, rather than anything too almond-shaped. Just avoid the temptation to go sock-free (trust us, you’ll regret it), and instead use this as an opportunity to make your socks as colourful as you dare.
Shetland Sweaters
Of course, the go-to preppy flex for any sweater is to wear one around your shoulders, with the arms tied just-so at your chest. And a Shetland wool sweater, a fixture on Ivy League campuses in the 1970s, will do all that, and go even further. Fuzzy but smart, light but super insulating, they’ll sit neatly over a button-down shirt, but work just as well chucked over a tee with a pair of chinos. Navy and grey might be the safer colour choices, but why not take the opportunity to introduce a little colour?
Braided Belts
When we said good preppy style is all about the details, this is what we meant. A braided belt, ideally in a good leather, will punch above its weight in bringing a fit together. Ideally, you’ll want a plainer style in black or brown, which will soon become fast friends with your chinos and jeans. Then consider swapping in a two-tone or more colourful style during the summer months. (Warmer days will return, I promise.)
Boat Shoes
Even if your only experience with boating is on vacation, a good pair of boat shoes is well worth the investment. They’ll sub in for your loafers all the way through the peak of summer, and hardier leather styles will still make a lot of sense in fall, too. There’s a raft of modern takes on the shape, often with sturdier tread soles, but there’s an equally strong case for a classic pair, especially when rendered in suede. (We’d throw in a good pair of ribbed socks here, especially if you’ll be wearing them with shorts.)
Rugby Shirts
While there’s a host of fashionably tweaked versions of the rugby shirt around – including some especially enviable styles at the most recent Celine show in Paris, which are guaranteed to become menswear-nerd catnip – we’re most excited by the thick, soft, often-striped rugby shirts emerging from some of our favorite off-runway brands. (Think J.Crew, Alex Mill, and KOTN, who even partnered with heritage rugby maker Barbarian to make its existing rugby even better.) Of course, nothing’s stopping you from wearing these with shorts and sneakers, but do consider tucking one into a pair of high-rise jeans, too.
Baseball Caps
There are a few distinctive design elements that’ll make a baseball cap feel more aligned to the preppy look (and, as a result, coordinate far more easily with the elements of a preppy wardrobe). In essence, you want a true baseball cap, rather than a trucker or camper style: look for six panel styles with a gently curved brim. Then, keep an eye out for gently retro touches: contrasting brims or embroidered branding. We’d probably advise against wearing insignia of a university you didn’t actually attend, though. Even if it is Ivy League.
Easy Tees
One of the secrets to preppy style is to make the smarter elements of your wardrobe look more relaxed, and the relaxed elements look smarter. A smartly proportioned tee in a neater, leaner shape will become your go-to for tucking into tailored pants, chinos, jeans and pretty much anything else with a waistline. We’d also co-sign on a thoughtfully-placed nod to Ivy League style: through sporting stripes, contrast hems at the neck and cuffs, or retro branding.
Sweater Vests
One of the great joys of a preppy sense of style is that it is, at heart, a little unserious. Take the sweater vest: there’s something charmingly irreverent about it (especially when it’s rendered in a classic Fair Isle pattern.) Make like Jeremy Allen White and throw one over a white t-shirt for “crisp-but-not-that-cold” weather, or layer it under blazers, cardigans, or even under shirting for a 1990s Polo and J.Crew vibe. Don’t overthink it. After all, we’re talking about a sweater with the sleeves removed. Unserious.
Deck Shoes
Consider the deck shoe a smarter upgrade on your trustiest sneaker: throw ‘em on, beat ‘em up, and where ’em with everything you’d otherwise rock with the latter. When in doubt, skew classic: brands like Sperry and Keds are pretty much synonymous with the style for a reason. Feel free to experiment with the whole Crayola’s box of colors, but you can’t go wrong with foolproof white, black, or navy.
