Saturday, September 12, 2026
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Buying a new pair of sneakers is a far more fraught experience than it should be these days. You want something comfortable, practical—and, yeah, a little bit cool. But your shoes shouldn’t be so cool that they make you look like you missed an update when the trend inevitably dies. Luckily, there are some truly timeless kicks out there, and we’ve rounded up a bunch of them. —Jonathan Evans, style director
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The world is awash in sneakers that are too fancy, too expensive, and too trendy. But there are pairs that will suit your needs perfectly. In fact, there are many.
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Traditionally, wearing sneakers meant one of two things: You were either working out or chilling out. They didn’t speak to your identity, or say much about your sense of style or standing in society. But now, in an age of casualization and comfort, your choice of sneakers and how you wear them speaks volumes. Thankfully, there are more options than ever, but that doesn’t necessarily make choosing any easier.
The rise and fall of the Adidas Samba encapsulates the challenge. Out of nowhere, the decades-old soccer shoe became an “it” shoe a couple of years back (and even earlier when you factor in the early adopters). If you were wearing Sambas, it meant you had your finger on the pulse. It also conveyed a certain reasonableness. We’re not talking about $1,000 designer sneakers, but classic indoor soccer shoes that cost a tenth of that.
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Gabriela Hearst’s men’s collections have a painterly quality about them, always rich in organic color and texture. Often they begin with methodical explorations of hues and patterns sketched in mountains of watercolor-filled notebooks that are strewn everywhere about her Manhattan HQ.
It’s only natural. Hearst was born in Uruguay and raised on a vast family ranch before she took off around the world, soaking in art along the way, and then settled in New York.
“People tell me, ‘Your colors are very South American,’ ” she says. “I think a lot of it has to do with the art that I was exposed to and, on the ranch, the most beautiful colors I’ve seen. The most beautiful skies. I’ve seen true beauty from a very young age.”
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My dad was a garbageman from Queens, hauling other people’s trash by day and flipping it online at night. By contrast, I’m a magazine editor, rolling up to a Manhattan skyscraper every day, where curation and items “priced upon request” are the coin of the realm. My dad bought his shoes at Payless; I’m writing this in Thom Browne oxfords in a stylish midtown loft I share with my fashion designer husband. We moved very differently through life.
I came out to my dad when I was 16, years before it was the status quo for high schoolers to come out at all. I was in my bedroom, cutting up a mix of Abercrombie & Fitch and Hollister shopping bags and taping them to my closet doors—plastering the room with aspirational sepia-toned photographs of sculpted male bodies. I was mid-decoupage when he stopped at the doorway and asked, without ceremony: “Are you gay?”
“Yup,” I blurted. I think I may have even laughed, gesturing vaguely at my room, as if to say, “Duh.”
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