Derek Jeter Looked the Part

Fashion
Our third Style Hall of Fame inductee knew what it meant to dress like the Captain.

In many ways, Derek Jeter seemed to exist outside time: the Yankees shortstop, sharp and elegant and effortless and winning, both on the diamond and off, could have slotted into a dozen different Yankees teams over the years. It’s only when you look at photos from his whole career that you realize the deep and unique ways he was a product of his time, with a sense of style simultaneously timeless and of its moment. That’s one reason he’s on the cover of our February issue—and (along with fellow inductees Allen Iverson and Deion Sanders) a member of the inaugural class of the GQ Sports Style Hall of Fame

A leisure suit is only complete with a two-way pager.

Arnaldo Magnani/Liaison via Getty Images

You can’t really talk about Jeter’s sense of style without talking about the pinstripes: his uniform, and the way he wore it. Boxy Yankees fitted perched on his head. Pants tight, even after it became fashionable to wear them baggy. Black high-top spikes, and a wristband on his left arm. There are vanishingly few ways to stand out on a baseball field; there are, somehow, even fewer paths to doing so on the Yankees, who still forbid long hair and beards. (“The Boss,” Jeter says of former Yankees owner George Steinbrenner in his Style History video, “was big on rules—he’d call down and have guys shave between innings.”) And yet Jeter conveyed something all his own: a crispness, a kind of style that colored inside the lines, that spoke quietly but wasn’t less expressive for it.

Things were similar off the field. Jeter, coming of age in the ‘90s, wore outfits that at first aged curiously, and in recent years have begun popping up in the cooler corners of downtown New York. Flowy trousers and tucked-in tees. White sneakers. An impressively restrained color palette. (Dare we suggest there’s something of The Row in his baggy “leisure suits” and vest-and-pants combos?) 

Three-piece suit minus the jacket and plus a tee: high degree of difficulty.

Richard Corkery/NY Daily News Archive via Getty Images

The oversized silhouettes were gone by the early 2000s, just as menswear was waking up to slimmer fits. (Longtime Jordan Brand athlete Jeter explains that many of his baggiest suits were the product of visiting MJ’s tailor.) And still, nothing really changed, in exactly the way that nothing about Derek Jeter—the important stuff, anyway—seems to decay with time. The suits were slimmer, sure, but they were still dark, slick, worn with purpose. There’s really only one way to dress, after all, when you’re the Captain.

Take a look at a few more of our favorite fits here, check out the full video, and make sure to snag a ticket to our inaugural Style Hall of Fame event, featuring Jeter and his fellow inductees in Arizona on February 11.

What a time!

KMazur/WireImage for Clear Channel Entertainment via Getty Images

Can’t beat blue jeans and white sneakers.

Arnaldo Magnani/Getty Images

Razor sharp.

Cindy Ord/Getty Images for Movado

2023 prediction: these non-suit suits are coming back.

Evan Agostini/ImageDirect via Getty Images

Hard to upstage Mo Vaughan, but a Rolex helps.

D. Kambouris/WireImage via Getty Images


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He was baseball’s unblemished victory machine—the savviest champ of his generation. And his icy-cool aesthetic defined an era. But if you thought Derek Jeter was gonna let loose once he left Yankee Stadium, then you don’t understand the much longer game he’s playing.

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