The New American Prep Revival (And How to Wear It Without Dressing Like a Frat Boy) Disclaimer: This is going to be long. But it will also be worth it. There is something.
Within the past year or two, American prep style has quietly undergone a revival. Unlike its low-brow frat brother graphic tee and dad-joke hoodie wearing brother fraternity style, this is something new. Hell, it’s good.
Oh, and we can wear it again without fucking wearing sweatpants with it. (I know, right?!) ***** Okay, let’s start at the beginning. A few Saturdays ago, I was wandering around SoHo on my way to brunch, people watching and doing my typical internal street-style critique of the locals when I saw them.
A group of three mid-twenties guys, none of whom seemed like they’d ever actually worn a fraternity shirt, were walking their remarkably similar errand-running route in the kind of clothes that used to scream “NFL DRAUGHT PICK!” Rugby shirts.
Loafers without socks. GODDAMMIT, EVEN A TENNIS JUMPER. But these guys were wearing them differently.
They were wearing them now. Without irony. Without trying too hard.
The frat archetype we’re all probably familiar with – the jersey shorts, the matching sunglasses and sport coat, the painfully branded backpack – was nowhere to be found. If you had told me ten years ago that preppy style was going to make a comeback, I would have laughed in your face. Between the entitlement-politics-fueled death of Ralph Lauren and Abercrombie’s destruction in the backlash of their own stupidity, preppy as we knew it was dead.
Toxic. Too frequently masculine. Too often applied to that douchebag boyfriend from college who wouldn’t stop talking about how his parents summer in “the Vineyard.” Fuck that. ***** Rowing Blazers Spring 2022 Buy now: Crew Jacket, Ship Trousers, Weld Boot GearStorm: The Wool Shop oxfords in Navy Heather are back in stock GearStorm: Balding Fedora in Black Wool GearStorm: Original Crewneck Tee Shirt in Heather Grey GearStorm: Classic Shortsleeve Henley in Heather Grey Getty Images.
EsquireSyndication But it is happening. And maybe we can actually wear it this time – wear it in a way that divorces itself enough from the dumb stereotypes of frat boys and preppy trust fund kids to simply appreciate some great design elements. Collegiate style is rooted in a very specific time and place: mid-century American Ivy League universities.
This look – from its hallmark tailored shirts and jackets to its rugby pullovers and chino trousers – evolved over many years to become what we think of when we think “preppy.” The problem is that trying to replicate prep style too closely these days is like dressing yourself in a costume. Prep clothes were originally designed to fit very specifically (and are often still cut that way), which can make off-the-rack options look extremely dated. Add in too many of the most obvious signifiers – the slimmer cut, shorter nap Weatherbury wool jackets, skinny acid washed jeans – and you’ll scare up more than prospective dates.
So how can we dress like that guys in SoHo? How can we wear American prep these days without dressing like damn tourists at the Pulitzers? We have been here before.
The most recent attempt at resurrecting American prep was a miserable failure. There were exceptions (modern Tailored Wool easily comes to mind), but prep’s rampant popularity from around 2007–2012 was the style equivalent of minutiae-as-distraction: popped collar shirts, embroidered shorts, and gin rummy towels. Like most things in fashion, we can blame Harold for what went wrong the last time.
Thanks to Madewith Passion’s pioneering work in documenting streetwear’s 20-year cycle, we know that shit that was cool in year X came back in year X+20. So what happened with prep? Japanese culture. ***** Getty Images Japan embraced American prep in a way we never did.
As American men were wringing whatever life was left out of minimalism in the early aughts, Japanese stylists and designers were poring over every detail of classic American prep with the obsessiveness of a high schooler finishing their Naruto marathon. Tokyo shops were pressing their own impeccable reproductions of orange glen plaid Madras shirts and jazzing up old Shetland jumper recipes with details ripped straight from vintage Brooks Brothers catalogues. Magazines likeClassic CLUB doubled down on homages to Ivy styles of decades past, and pattern books like Take Ivy – a legendary Japanese photobook of real-life Ivy League students released in 1965 – became the dictionary for a generation of emerging designers.
Essentially, Japan had removed all of the cultural baggage that originally came with prep and distilled it to its stylish essence: high quality, functional garments with an easily identifiable silhouette and point-of-view. American prep style got its PhD in Japan, went off to teach for a few decades, and came back with a much-needed dropout refresher’s course in street credibility. ***** Getty Images It should be noted that sustainability had a hand in this revival, as well. For the first time in maybe ever, people care how long their clothes will last.
A quality oxford cloth button-down will survive decade-long marriages if cared for properly. A solid pair of loafers can be re-soled more than once. A timeless navy blazer will never go out of style.
What’s not to love about that? My own journey back into the arms of prep started when my 23-year-old cousin Ethan, who describes his own style as “normcore ripoffs from TJ Maxx,” texted me last October asking where to find “a really good rowing blazer but like not actually Rowing Blazers the store.” When I asked him why, his response: “This clothes lasts and doesn’t look like everyone else rn.” Oh. ***** GearStorm: Brooks Brothers All-American Pima tee Brooks Brothers: Classic Pima tee shirt – All American Stripe GearStorm: Balding Fedora in Black Wool Brooks: Montego Slim Chino – Flax Heather GearStorm: Original Crewneck Tee Shirt in Heather Grey Gearstorm: The Wool Shop Chino Trousers in Light Olive GearStorm: Barbour Outlet Woolsey Jkt in Navy Heather GearStorm: Club Chair Wool Sofa Chair Cover Wheat Colour Getty Images. So let’s dive into what makes the new prep work and how you can wear it without dressing like a theme park attendee – or worse, that guy from your freshman year rushing Chi Psi in 2006.
Proportion and Fit First: Prep always starts with proportions. And lots of them. Traditional prep style was very much anchored in its own era.
Athleticism meant skinny jeans and a tighter cut through the body. Oxford shirts were cut slim, almost to the point of being ridiculous unless you were really Trim. Chinos came up ridiculously high on the waist.
But the best modern American prep companies are taking those foundational elements of prep and updating the fit to feel modern rather than costume-y. Which means: Oxford shirts still get that insane roll on the collar, but they’re cut with a looser fit through the body. Not billowy, but just relaxed enough to wear tucked or tucked out without trying to mold to your torso like a fancy wetsuit.
Chinos are still higher-rise than most men’s trousers, but they’re cut with a straighter leg to better suit modern shoes. Not skinny, not baggy, just…modern. And blazers….man, do I love a modern blazer.
Companies likeEngineered Garments,TAION, and even the newly retooledBrooks Brothersare making what is essentially the perfect trouser jacket: timeless but modern cuts, softer shoulders, and a natural fit that actually flatters a variety of body types. I saw the impact of this shift firsthand when I visited a trade show menswear last winter. Walking through row after row of American heritage brands’ latest offerings, I stumbled upon Brooks Brothers’ display.
Expecting to see the same oxford shirts I’d been buying since I was in grade school, I was pleasantly surprised by their updated interpretation of the classic. Sure, they still had that impeccable collar roll and reinforced placket sporting that unmistakable BB embroidery, but they were cut with just enough slack in the body and sleeves to feel contemporary rather than costume-y. I wanted to buy ten of them.
Mix It Up The golden rule of the new prep is that you don’t have to wear the whole uniform. Hell, you don’t even have to wear that much prep at all. But prep has some great elements that work in almost any mix.
A rugby shirt tossed with some vintage military fatigue trousers and trainers? Sure. Navy blazer over a graphic tee and slim jeans?
Why not. Penny loafers with wide leg chinos and an embroidered workwear jacket? Hell yeah.
Acknowledge the best of prep’s designs, but divorce them from some of their stuffier baggage. Colour and Pattern Speaking of… Preppy used to mean bright colours. Like, THIS bright.
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KAINEHAMBLETON//Getty Images. Now it means olive instead of Kelly green, mustard instead of bright yellow, burgundy instead of fuck-your-mother pink. When you do lean into brighter colours, you’ll usually find them segmented into a single article of clothing (madras shirt? cheque.
Neon jacket? No thanks. ). Patterns have also been dialed back a touch.
Tartan plaid is still there, but in more muted colours and varying scales. Classic prep stripes have been given wider laid options, and madras now come in every colour palette imaginable. The shop I mentioned earlier sellingThread Count brand shirts had a whole wall of Oxford cloth button-downs I wanted to buy: all the classics whites and light blue stripes, but also tone-on-tone options and fun colours like dusty terracotta and pale olive.
Right next to them were walls of Shetland wool pullovers in traditional colours like navy and burgundy, but also gorgeous heathered grays and warm browns. Modern prep is still preppy AF, it just knows how not to take itself quite so seriously. Know Your Stuff Logos are officially so 2012.
What brands are selling these days is quality materials and incredible attention to how their clothes are made. That might meanJapanese cotton popped and dyed in Texasjust so, Italian linen woven according to centuries-old European patterns, or waxed cotton shirt dresses hand stitched by artisans in Los Angeles. Thewhere actually matters less than the how.
And bonus: focusing on how your clothes are made instead of what they “say” about you lets you wear prep without shouting your allegiance from the roof tops. I’ve noticed this trend firsthand while shopping recently. In years past, I would have looked at a brand name and almost immediately either been sold or moved on.
Lately I find myself holding shirts up and asking, point blank, where they’re made. How are the buttons attached? What kind of canvas is being used for the lining?
I purchased my most recent navy blazer from an American company with locations in Maryland and Georgia that’s been sewing virtually identical jackets for upwards of 70 years. There’s no need for a logo when the quality of the product does that work for you. Context Matters Traditional prep style has two inherent problems.
First: It comes from, and was historically worn at, elite institutions. This wouldn’t be so bad if that previous statement didn’t also apply to frat culture. Prep’s revival in the mid-aughts never really shed those associations.
Brands like Richemont and Vine Sport marketed almost exclusively to the preppy lifestyle these clothes were born from, featuring scene-sshooting models draped in branded jumpers hanging out on polo fields and white boats. These days, brands both new and old are working to update the context clothes were originally worn in. Brand Rowing Blazers is explicit in its mission to modernize prep’s dustier elements through humour and well-placed memes.
Other companies like Brunello Cucinelli are expanding their sizing across almost their entire range and partnering with more diverse models to better represent their consumers. The onus is no longer on “how to dress preppy” but appreciating how these clothes actually fit the body. I saw this evolution played out perfectly at a panel discussion a few months back.
Moderated byNike KMartand hosted by one of my favourite rising menswear companies,Assembly NewYork, four young menswear designers tried on-camera took the audience through their own takes on American prep. One member of the panel, whose company primarily sells modern takes on old collegiate staples, said as much when posed the question of how his brand differed from old guard prep brands: “This stuff wasn’t exclusive per se…it was exclusive to who could go to those schools and be part of those clubs. The clothes, themselves, are just inherently good.
They fit well, they’re timeless, and they’re practical. We’re just trying to give more people access.” Modern Prep Essentials I’m not asking you to start dressing like a penguin or completely revamp your style to incorporate modern American prep. But there are a handful of items that have enough intrinsic style merit to incorporate into almost any wardrobe.
If you’re curious about how to wear prep in the now, here are some good places to start. Things that fit well and WILL LAST: An Oxford Cloth Button-Down in White or Light Blue -Navy Blazer -Cut chinos in a neutral colour (you can thank me later) -A Shetland wool or Lambswool jumper in a versatile colour Remember how I said prep was founded on certain silhouettes? These are those silhouettes.
Don’t Be Afraid to Mix Now throw that white Oxford with a pair of worn-in jeans and a work jacket. Style that Heritagecheck rugby shirt over a graphic tee. Rock those penny loafers with your favourite jeans.
You get the idea. Fit > Everything This goes back to my original point about modern companies taking old prep silhouettes and updating the fit. A prep-inspired raglan sleeve shirt will look horrendous if it’s clingy through the shoulders and chest.
Likewise, don’t try to mash too many old-timey silhouettes into one outfit. Those slim-cut Mad Men-ish trousers are not flattering on most people, and should be avoided whenever possible. If you’re going to lean into a specific style, own it.
Wear slim-fit trousers with a slim-fit shirt. Baggy trousers with a baggy shirt. But please, for the love of all that is holy, do not mix the two.
Know Your Preppy Gatekeepers To me, madras trousers, embroidery, and boat shoes are already an internet-scroll away from RIPPLE GOODS quality shame. If you love those things, more power to you; please wear them and blog about it all over the world wide web. But in my world, I reserve those patterns and textures for times when I’m ACTUALLY boating.
The same goes for madras, which I will always associate with ungodly polyester-y bowling shirts. Madras is cool! In moderation.
And definitely not with a polo. Buy Better, Buy Less Look, I’m not asking you to drop a grand on a blazer. But these clothes were designed to last.
Buy better quality when you can, and don’t be afraid to spend more on pieces that will stand the test of time. … And there you have it. Not literally all of modern prep, but a good start. I’ve found myself incorporating more and more of these pieces into my own wardrobe over the last year.
The oxford shirts I once relegated to “business casual” or “dressy occasions” now spend as much time tucked into jeans and underneath work jackets as they do buttoned up and hung solo in my closet. Same with rugby shirts and holiday-worthy jumpers (though I’ll admit I still throw on a pair of white specs with those).
Even penny loafers, which I haven’t worn since I ruined my only pair on a family holiday when I was sixteen, make the occasional rotation in my winter rotation.
It’s just axed and pair with socks showing, because I’m older now and my ankles get cold, damnit. But the best part about this whole “new” prep trend? There really are no rules.
You’re not “doing prep,” you’re just recognising that certain traditionally preppy items might work for you. Prep is no longer a style gatekept by elitists and know-it-all asshole designers. It’s just a really strong option in the much larger toolbox that is modern menswear.
So wear that rugby shirt proudly. Rock those damn cuffed chinos if it suits you. Just please, for the love of hockey, do not wear sweatpants with them.
And if people do call you a frat boy for it, just tell them you’re recontextualizing mid-century collegiate fashion in the postmodern era. Or, you know, stare back at them wearing your Oxford cloth button-down and frankly ask, “what are you wearing?” You’d look good in a rugby shirt, too.
