5 Ways to Wear Modern Prep No Matter Your Style

Turns out the classic style can fit in just about anywhere.

Long gone are the days when preppy style was relegated to East Coast boarding schools and 1980s John Hughes movies. Today, classic prep has found its way into almost every way of dressing. From street style (Supreme x Lacoste, anyone?), to athleisure to downtown chic, modern prep is everywhere. But just in case you haven’t found your way onto the bandwagon, here's an easy primer for adding a dose of prep-school cool to practically any look. From pastels to nautical themes to the power of a polo shirt, welcome to Modern Prep 101. 

1 The Button-Down Type 

Nothing says prep like a pair of chinos and an Oxford shirt—two stalwarts that are likely to be in any classic dresser's closet. To really nail the preppy version, however, stick with light tones for the shirt (extra points for stripes) and off-white or light khaki for the chinos. Then add a woven belt for texture and a patterned bomber for some pop. Top it all off with that king of preppy footwear—the 2-eyed Sperry boat shoe.


Authentic Original 2-eye boat shoe by Sperry, sperry.com; Leonard chino in eggshell by Billy Reid, billyreid.com; navy rinsed fine stripe one-pocket shirt by Buck Mason, buckmason.com; checked cotton bomber jacket by Barena Venezia, matchesfashion.com; Gael belt in caramel by A.P.C., needsupply.com


2 The Athletic Type 

For the guy who always looks ready for a quick game of pick-up football, a striped tee and a pair of linen shorts are stylish, warm-weather must-haves. They’re great for any sort of active lifestyle, and they're a solid foundation for any summer wardrobe. Luckily, adding some preppy style to this is extremely easy. All you need to do is splash on some nautical flair courtesy of a pair of white canvas sneakers, and, once the temperatures dip in the evening, a bright red windbreaker. It’s a look that will get you into any Kennedy compound on the Eastern Seaboard.

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Captain’s CVO sneaker by Sperry, sperry.com; Baxter stretch linen and cotton-blend shorts by Club Monaco, mrporter.com; 1525 long-sleeved Loctudy striped tee by Armor-Lux, endclothing.com; red cotton twill jacket by Polo Ralph Lauren, ralphlauren.com; Clubmaster acetate and gold-tone sunglasses by Ray-Ban, mrporter.com 


3 The Laid-Back

Beach Bum  For the casual, California surfer type, it’s tough to beat a pair of linen pants and a light cotton shirt for those long days of summer. And of course, let’s not forget the flip-flops. But while the chill vibe might seem a long way from the classic preppy style of the East Coast, it’s not impossible to marry the two: Stick with pastel hues for the linen pants, and then try a collared popover shirt for the top. And finally, for the preppy piece de resistance, add a sherbet-hued seersucker hat.

Authentic Original flip-flop by Sperry, sperry.com; Verano Beach Pant by Outerknown, outerknown.com; short-sleeve Italian indigo stripe popover shirt by Todd Snyder, toddsnyder.com; seersucker 6-panel cotton hat by Noah, noahny.com 



4 The Fashion-Forward Type 

For those nattier dressers who love mixing patterns and focusing on the finer details, the idea of preppy style might seem a little unadventurous. But it's an easy problem to solve. For one thing, a pair of two-toned boat shoes are both preppy and dapper at the same time. And to accomplish a more fashion-forward look that still has that dose of prep, simply mix a patterned cardigan in muted shades with a pair of plaid trousers. Finally, finish the whole thing off with that preppiest of preppy shirts—the pastel polo.

Gold Authentic Original 2-eye Chevre boat shoe by Sperry, sperry.com; plaid straight leg trousers by Incotex, farfetch.com; Caviar pique polo shirt by Lacoste, lacoste.com; leather-trimmed canvas briefcase by Bleu de Chauffe, mrporter.com 


5 The Downtown Type 


Crisp and dark are probably the two most important style markers of the downtown denizen. Luckily, preppy style can slide easily into this look. Stick with the classic urban uniform of dark raw indigo jeans, a crisp white Oxford, and leather loafers, and then add a dose of boarding school prep with a gold-buttoned navy blazer. It's subtle and snazzy all at once.

Essex penny loafer by Sperry, sperry.com; The Henley jean in raw selvedge indigo by Baldwin, baldwin.co; white Japanese slim-fit Oxford by Everlane, everlane.com; classic single-breasted sport coat in Super 120s twill by Thom Browne, farfetch.com; Metro Datum Gangreserve 37mm Stainless Steel And Leather Watch by Nomos Glashutte, mrporter.com 

This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.

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Scott Christian
Scott Christian is a style writer for Esquire.com
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