Yesterday morning, I woke up and did something I haven’t done in nine months. I threw on a pair of sneakers. My weathered, white Tretorn Nylites felt right with my slim khaki chinos, black crewneck sweater and thin-striped button-down. Though this geezer-steez move is ubiquitous in certain preppy circles of the fashion world, I never knew how easy it is to pull of until I strolled down 15th Avenue.
Most people wear sneakers all wrong. Part of it boils down to sneaker choice; part of it is what they’re paired with. That said, there are basic rules of sneaker wearing to follow to ensure that you exude a subversive preppy vibe instead of presenting a schlubby, clueless appearance.
When in doubt, trust New Balance: They’re made in the USA, and their clunky profiles are both outre and sexy. New Balance shoes often come in muted or ostentatious colorways, so they’re a great accessory to liven up a classic outfit.
Wear white after Labor Day: Wearing white after Labor Day was once considered a cardinal sin in the fashion world, but why not wear white shoes year round? My beat-up Tretorns look best in the fall, where their faded, stained patina pops out against the maroons and golds of the leaves. If you regularly clean and polish your white sneakers, breaking this rule will be a little more difficult, but still doable.
Nikes are meant for the gym: I don’t care how much you love your Flyknits or Air Jordans, but their recherche neon hues and space-age profiles aren’t suited for the street. I own a pair of Nike gym shoes, but they never see the street unless I’m engaging in extra physical activity during my normal daily routine. Too many people wear them with suits, a heinous look. If I were the fashion police, I would perform a citizen’s arrest on these sartorial criminals.
Choose your pants wisely: Sneakers with jeans is too obvious of a pairing, unless they’re a variation on the same color. Wearing sneakers with cords or chinos creates just enough of a clash to make an outfit attractive and intriguing, and dresses down the pants without making them look unprofessional. Cuffing said pants adds a dash of calculated, professorial nerdiness to the ensemble.
