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A Man's Guide on How to Wear Sneakers with Everything

A Man's Guide on How to Wear Sneakers with Everything

25 Sep 2020

A Man's Guide on How to Wear Sneakers with Everything

By James Shackell

Put your feet up and get comfortable—we’re talking sneakers today. Now there are some misconceptions around how to wear sneakers, particularly when it comes to suits and smart casual attire. And that’s because not all sneakers are created equal. There’s a world of difference between well-kept, leather-lined white sneakers (like these) and your old pair of Volleys with the mysterious green stains around the toe. One pair is totally acceptable for dates, smart casual cocktail parties and meeting your mother-in-law, the other one…not so much.

Here’s our ultimate crash course in how to style sneakers for any occasion.  

When to Wear Sneakers

The rules around sneakers have definitely relaxed over the last ten years. Matching your formal outfit with sneakers, or hiding some tan leather trainers under a sharp grey suit, is not the fashion crime it used to be. The beauty of good-quality, smart-casual sneakers (and we can’t stress the ‘quality’ bit enough) is that they instantly knock the starch out of anything. And that’s great for occasions where the full three-piece suit and brogues might be a bit much: family lunches and Friday date nights, in particular. Think of men’s sneakers as the mullet of the smart-casual world: business on top, party on the bottom.

When NOT to Wear Sneakers

While you can almost wear sneakers with anything, to anywhere, there are still some occasions when it’s best to leave them in the wardrobe, especially if they're in need of a good clean. Job interviews are the big one, unless you’re going for a job at some Silicon Valley tech start-up…and even then it’s a bit of a gamble. A solid pair of leather loafers or Oxfords is going to be your best bet for any truly formal occasion. Obviously ‘Black Tie’ events are another good example. If you’re wearing a black satin tuxedo, it’s highly unlikely you’ll be able to find sneakers to match.  

How to Style Sneakers

A solid pair of white sneakers has basically become a wardrobe staple over the last few years, and that’s really because they match well with anything. We’ve written an entire article on how to style white sneakers, but here are the cliff notes: you can either wear cropped pants (or cuff your ankles), or head down the athleisure route, which requires tapered joggers, crew neck tees and bomber jackets. The whole point of sneakers is to attract attention down there (nope, further down), so a high cuff really helps sharpen that silhouette and show off your socks (or ankles with something no show).

Wearing Sneakers with Jeans

Jeans and sneakers are the sartorial equivalent of strawberries and cream. You don’t need us to tell you that they belong together. But there are a few things to keep in mind when styling your favourite denim. First is colour. Do you want a chunky white sneaker outfit, or something more interesting? Forest green leather sneakers or khaki suede sneakers both match well with blue jeans. The second is cut. Baggy jeans with sneakers hasn’t been a good look since Clueless came out. You want a high cuff and a tapered leg (it doesn’t have to be painted-on-skinny, just something clean and neat).

Wearing Sneakers with Suits

Whole books have been written on styling sneakers with suits (we’ve written a little something ourselves, over here). Smart casual sneakers under a sharp blue or grey suit is definitely one of our favourite preppy looks, but there are a few things to watch out for. One thing some guys get wrong is trying to do too much with their sneaker-suit combo. Stick to classic, block colours: white, black, navy and tan are the obvious candidates. Next, think about combinations. A black pinstripe suit probably won’t mesh with khaki green sneakers (this is why white sneakers are such a god-send, they go with basically everything). Finally, focus on the cut. Sneakers give suits an edge, but there’s only so much edge you can give a chunky, unflattering, badly-fitted suit jacket. Go for a slim-fit jacket, and make sure your pant legs are crisp, straight, and cuffed appropriately (not too high, but not too low either).

At the end of the day, how to style sneakers, and when to where them, is totally up to you. There are hundreds of great outfits for sneakers. The trick is confidence: playing around and experimenting until you find something that feel right.