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Suit with Sneakers: 3 Foolproof Ways to Dress Down Your Tailoring in 2022

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The idea of wearing a suit with sneakers was once a radical, clutched-pearls-inducing departure from menswear convention, but these days, it’s practically de rigueur—especially when dress codes skew so lax opting to wear a suit at all means you’re miles ahead of the competition. In 2022, showing up anywhere in a suit is kind of a radical proposition. So it follows that the guidelines around dressing down your tailoring are a whole lot looser than five years ago. (FYI: so is the tailoring). But there’s still a few helpful tricks to make sure everyone knows you’re doing it as a purposeful swerve and not because you’re, like, a first-year associate hoofing it to the courthouse before a big case.

The basic tenets aren’t all that unexpected. The real secret? Understanding that sneakers generally pair best with suits that are already a little more chilled-out. (Sorry, Pitti Uomo peacocks: if your feet are crying out for a pair of Nikes, leave that strong-shouldered bespoke number at home.) Sure, it helps to wear sneakers that complement the color of your tailoring, but they should sync up with your suit’s proportions too: slim suit = slim sneakers; big suit = big sneakers. Generally speaking, the more relaxed the silhouette the more opportunity you have to freak your footwear—though, yes, sleek, streamlined kicks will nearly always work.

Confused? Don’t be. Because we’ve consolidated the type of tailoring-friendly sneakers you should be thinking about right now into three general categories. All of the below are foolproof options—the ideal finishing touch to an outfit that might include a camp collar shirt, a knit polo, or a threadbare vintage tee. The next time your hard-bottoms need a break, you know where to turn.

The Can’t-Miss Classics

Wear With: A Slim, Slightly Slouchy Suit (and Everything Else, Too)

As classic as a Dieter Rams-designed calculator and nearly as functional, these are the perennial stalwarts you can always turn to when suiting up—legendary sneakers you should already own that have earned their right to be worn with whatever the hell you want. The secret to their versatility? Limited color palettes (lots of black, white, and, uh, black and white) and no-frills silhouettes. Wear these with your regular ol’ suit pants, no matter how precisely tailored. Bonus points if your trousers have an ever-so-gentle break. 

Converse Chuck 70 sneakers

Adidas Samba classic sneakers

Vans core classic slip-on sneakers

The Bold ‘n Bulky Kicks

Wear With: A Big, Baggy Suit That’s Up for the Challenge

As is the case with most style “rules,” there’s room for this one to be broken. So while clean, classic kicks are a great entry point, if done right their chunkier counterparts—ones with serious heft, color, and ankle-supporting tech—can take you from red carpet hero to runway god just as ably. Naturally, Rocky’s wearing a rarified pair of since sold out Dior sneakers up top, but New Balances offer the same effect—just be sure to pair them with wider trousers that anchor the shoe’s bulk. And if ever there was ever a time to layer a mesh-y tank under your suit jacket, this is it.

Asics Gel Kayano 14 sneakers

Balenciaga Track 2 caged sneakers

The Loafer-Sneaker Hybrids

Wear With: A Very Right-Now ‘80s-Inspired Suit

Okay, we’re cheating here: these loafer-sneaker hybrids hardly constitute the purest version of the form. But if you’re having a hard time wrapping your head around the idea of wearing your basketball kicks with a swanky double-breasted suit (unless your Adam Sandler, don’t), they represent the ideal middle ground. Plopping elegant leather uppers on top of comfortable rubber soles is an easy way to ape the look without rocking the boat. (As far as shoes that evoke the yachting life go, though, these are pretty high up there.) Wear them with a suit that’d make an ‘80s-era Miami tough guy proud—think: stronger shoulders, a chilled-out cut, and wide, high-waisted trousers that shrug at any and all dress code conventions.

Loro Piana summer walk suede loafers

Fear of God croc effect leather espadrilles

Woolrich spring slip-on shoes

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