See the guy on train station platform with his gray suit and New Balance running shoes, which – like Melanie Griffith in Working Girl – he wears exclusively for his commute? Or see the eminent graybeard in your workplace, the gentleman who believes, with some justification, that he has earned the right to wear a dark pinstriped suit with an especially horsey pair of Under Armour SpeedForm Geminis?
OK, forget those guys, because they're doing things ineptly.
The new-look luxury
Once upon a time, the suit-and-sneakers combo was primarily adopted by narrow subsets of the male population, such as self-conscious rebels wearing Converse Chuck Taylors to homecoming dances. Also, victims of chronic ankle pain.
But no longer. "Sneakers with a suit is the big trend right now," says Loris Spadaccini, vice-president in charge of the men's division at M. Gemi, which sells Italian shoes directly to consumers. "It's accepted even in traditional business environments." He ventures further that the craftsmanship of high-end shoemakers – "our uppers are not glued but stitched to the sole" – has helped to facilitate the acceptance.
Now, instead, look at this trendy young guy with the hem of the tiny trousers of his bright blue suit hovering a full three inches above the green heel tabs of his box-fresh Adidas Stan Smiths. You can quarrel with the tailoring, but the guy is on to something. The relaxed jackets of the moment, with their unstructured shoulders and unfussy attitudes, are mainstreaming the sneakerhead ethos to memorable effect.
A statement shoe
Consider the testimony of Sébastien Kopp, who 12 years ago co-founded the French sneaker company Veja. "When we created the brand, we never imagined someone wearing sneakers with a suit," Kopp says. "But we've seen it across the board, from businessmen to artists to TV personalities. It works best when the shoe pops and is quite visible. It shouldn't be subtle, but rather make a statement."
Well-dressed men intuit this, as I discovered the other day loitering on West 55th Street in Midtown Manhattan. The flashy casual kicks worn by executives and aspirants confirmed that we have plunged feet first into a new era.
They tended to observe what is, though not an ironclad law, a smart guideline: Use contrast to make a suit-with-sneakers outfit sing. Their sedate medium-toned suits were paired with sneakers that split the difference between wine-dark opulence and pumpkin-bright flamboyance, sporting what looked like suede babies from Bottega Veneta with the intrecciato motif, rich brown Zegna Pella Tessutas with a similar weave, and ultra-lightweight, napa-calf low-tops from A. Testoni.
Decoding the code
Spadaccini specifically advocates for the white sneaker to go with a blue suit: "We like this idea of high contrast to make footwear the centrepiece of the outfit," he says. It's a low-degree-of-difficulty move: Match the resort-hotel airiness of a perforated leather court shoe against the citified solidity of a solid suit.
A somewhat riskier-and, therefore, potentially more rewarding-move is to juxtapose the earth tones of khaki with the space-suit silver gleam of metallic trainers. And though high tops can be highly tricky in this arena, a pair will perfectly accessorise with a skinny dark suit in certain contexts, such as overpriced nightclubs and televised music-industry award shows.
In the best such pairings, the sneakers in play are proud of their sneakerness, I believe. They might be elevated-by way of the quality of the leather, the stitching, the shoelaces-and they might be minimalist, with a light touch on multicoloured trademarks and lavish logos. But they don't shy away from being, in a fundamental way, sneakers.
Embrace the comfort
Ironically, a sneaker that too closely resembles a dress shoe looks worse in most cases. A black slip-on sneaker, for example, can sometimes assume the sad aspect of an orthopedic loafer.
Once you embrace the spryness of the ensemble, you can explore the versatility of the look. Years ago, on the day of my bachelor party, I wore a seersucker suit, a blue polo shirt, and a pair of Adidas Rod Lavers from the Belmont Stakes to Wolfgang's Steakhouse. You can go anywhere in such an outfit-and go there faster than you can in other kinds of shoes. I suggest trying a lightweight suit with a flashy pair of kicks at a beach wedding, where you'll appreciate the extra traction, especially if you get cold feet and sprint away from the altar at the last second.
Check out the gallery above for a selection of the best suit-worthy sneakers.