It’s best we start by coming to grips with it first, sneakerheads: no matter how much you love your sneakers, respecting the dress code is always more important than rocking your kicks. If you’re attending a formal event, taking your girl out to a fancy place, or if your job demands it, a suit must be a suit, and formal clothes must always be worn with appropriate shoes, which, 99 percent of the time, means dress shoes. That’s a rule that takes a level of finesse to break without falling apart. Rubber shoes for casual, leather shoes for formal—even your grade school principal can tell you that.
The problem, of course, is that you’re a sneakerhead, and you want the whole world to know it. You’re used to a graphic T-shirt and jeans, a snapback or a five-panel, and one of those Rastaclat bracelets plus your G-Shock to match. Because of your oh-so-subversive tastes and creative-class millennial sensibilities, you aren’t accustomed to oxford button-downs or pleated pants or even the notion of tucking your shirt in—no, you save those for the tools who refer to themselves as dapper gentlemen (admittedly, these guys are, in fact, tools). You’re caught up in your need to showcase your sartorial irreverence, your need to disregard the rules in favor of expressing yourself. So you commit the incredibly unfortunate mistake of wearing your Air Jordans to your cousin’s wedding. They match the corsage, don’t they? It makes sense, at first, because you’re a sneakerhead—but an honest look in the mirror should convince you otherwise.
The truth—that every sneakerhead must come to terms with as they come of age—is no, most of your Jordans don’t look good with a suit. Neither do your Air Max 90s and your Dunk SBs; nor your Ultra Boosts and NMDs. Make no mistake: That’s not to say that these are inherently bad sneakers, or that anything rubber-soled is off-limits to formalwear—it’s just that these particular shoes aren’t designed for that. They just do not look good for that kind of outfit. In fact most sneakerhead favorites look incredible with jeans or joggers, but are terribly inappropriate under suit trousers. Resist temptation. Do not wear these kinds of sneakers with a suit.
But once you do learn to accept this; once you realize that there are boundaries, you can begin to foray back into the notion. Consider, first, the occasion: Is this a church wedding, or a garden wedding? Are you attending a formal corporate function, or the Star Magic Ball? If you find that the event is casual enough to leave a little room to add some flare to your outfit, maybe sneakers would be acceptable.
Then consider the suit you intend to wear. Specifically, consider how it fits. Sneakers are best worn with slim trousers that don’t break (that is, mej bitin pants that, while standing up straight, don’t touch your shoes, and even show a little bit of sock). Then, like your favorite jeans, it helps to tailor your suit pants to have a little taper, which means the width gets slimmer from top to bottom. Just be careful not to make your suit pants too skinny, though; they’re not jeans, so leave a little room for your nuts and thighs to breathe. It helps to work with your tailor to get the just-right fit.
Then, and most importantly, consider which sneakers to wear. This is the most crucial. The rule remains: no basketball shoes, no Air Max, none of that ostentatious (and otherwise cool-looking) stuff. Just because your Space Jam 11s are done up in shiny black patent leather doesn’t mean you get to wear them for formal outfits. What matters here is the silhouette: the overall shape of the shoe and how it looks on feet; that it is slim and minimal. Less chunk, less features, less details, less colors, less contrast, less branding—less of everything. Consider also materials: fine full-grain leather and suede are acceptable; anything with plastic panels or sports mesh is not.
Here are a few of your best bets:
Vans OG Leather Old Skool LX
Common Projects Achilles
adidas Stan Smith Collegiate Navy
Onitsuka Tiger Mexico Delegation
New Balance M576
Epaulet German Army Trainers
Notice the common threads that bind these sneakers: they’re often sleek, slim, and understated in shape. They don’t have as many lines and as much structure as the sneakers you know and love, and save for the New Balance M576 and the Vans Old Skools, branding is almost unnoticeable. Most are also done in incredible materials with great craftsmanship—constants when it comes to dressing sharp. Let these examples inform your choice of sneakers that you can pair with a suit. There are certainly a lot that can make it work—you just need to know how to spot them.