There’s a deliciously anticipated moment with certain types of clothes when they reach fleeting perfection a second before they fall apart forever. This is especially true of chinos. Not the stretchy, non-iron ones you might be thinking about but proper chinos. Made from cotton that starts with an almost cardboard-like consistency, they shed fibers with each wash as they mature inexorably and beautifully toward their own oblivion. But along the way? They just get better and better until they’re damn near perfect.
James Dean hanging loose in 1955.
The problem is, it’s getting devilishly hard to find a pair that starts out with the right DNA. When Steve McQueen attempted to leap over a barbwire fence in The Great Escape, was he wearing stretch chinos? No sir. He may have taken personal liberties with the cut, favoring a slimmed-down ’60s fit over the baggy military-issue pants of the ’40s, but the cloth at least was the Real McCoy. When young JFK went on his sailboat, did he wear skimpy non-iron trousers? Nope. But neither he nor McQueen had much of a choice. Chinos just weren’t made that way back in the day.
Overcoat ($690) and shirt ($495) by Isabel Marant; chinos ($200) by Dockers; boots ($1,365) by Marsèll; ring ($71) by Chrishabana; earrings ($1,195) by John Hardy.
Nowadays, though, the algorithms of mass fashion have decided for us that we prefer elastane-enriched, shrunken facsimiles of the great American chino over the real thing. So we are bombarded on social media platforms with ads for skinny, flimsy, stretchy, wrinkle-free pants that will never, can never, attain sartorial nirvana. They may hug your butt in all the right ways—but they do you no favors in terms of style.
Left: JFK aboard his sailboat, the Manitou. Right: Miles Davis taking a break in chinos with room to move.
The thing to do, in very American fashion, is rebel. Reject the subpar options that get served up to you and instead go out there and hunt for the genuine article. A great pair of chinos should be made from heavy cotton and pay homage to its standard-issue roots, with a generous cut that gives no hint of whether you’ve been skipping leg day. You could dress it up with a crease down the front. But it’ll look far happier worn unironed as the most relaxed part of your outfit, especially when you throw on a blazer.
Jacket ($420), shirt ($245), and chinos ($195) by NN.07; shoes ($895) by Marsèll; Mechanic 39mm watch ($1,500) by Shinola; heishi bracelet ($695) and chain bracelet ($7,500) by John Hardy; socks ($12) by Stance.
Once you’ve found yours, wear the hell out of them. And invest in multiples. Start them in stages and you’ll always have a pair or two approaching perfection. They’ll feel so good that you won’t ever give a second thought to how your butt looks in them.
Shop Chinos
Dockers x Transnomadica Pant
Photographs by Ryan Slack
Styling: Alfonso Fernández Navas and Andrea Rios
Grooming: Devra Kinery
Models: Sam Pearce at Next Mangement; Osman Cessay at Marilyn NY
This article appeared in the April/May 2025 issue of Esquire
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