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In the pantheon of can I pull it off? the sweater vest is especially perplexing. “What is this for?” we ask as we stare at the enigmatic, sleeveless wonder once considered fuddy-duddy even for the most classics-professor-ish classics professor. It wasn’t always so—in fact, the sweater vest was once the province of jocks.
In menswear, it dates back at least to 1907, when University of Michigan football players were awarded versions with an embroidered M to celebrate their on-field achievements. It was downright chic around the jazz age—certainly Jay Gatsby would’ve had one or five in his closet—but became the mark of the geek by midcentury, adopted by grandpas and fusty academics. Since then it has at times swung back into fashion—the Ralph Lauren–clad, prepster-studded ’80s were a particularly good patch—but by the early 21st century the standard-bearer had become none other than Rick Santorum. Generally, like short-sleeved button- downs and tortoiseshell glasses, it was planted firmly in the nerd style canon.
These days, the best sweater-vest deployments are more skate god than Brit-lit major.
Though the sweater vest trailed those other two by a few years, all three have come smashing into the zeitgeist looking pretty freakin’ great—especially the sleeveless wonder. In recent years, we’ve seen Ryan Gosling; Tyler, the Creator; and Harry Styles rock one on the regular. You can, too. Checkered (or should I say argyled?) as its past may be, this not-so-humble piece of knitwear is now a straight shot to standing out in a crowd. You just need to decide how it fits into your own wardrobe.
First of all, this is not an arena in which to fear a little breathing room. Letting it hang loose is crucial in mitigating all that stuffiness. We’re no longer layering with repp ties and flat-front chinos tailor-made for the Class of ’83 Alumni Bash. These days, the best sweater-vest deployments are more skate god than Brit-lit major. This means pairing yours with slouchy trousers, bucket hats, and well-worn sneakers. And since it warms your core while leaving your limbs cool, you’ll want to employ it as a hero piece during that strange transitional period when the forecast basically reads “???” Once it cools down, the sweater vest becomes a layering MVP; it looks just as sharp under blazers and bombers as your favorite merino sweater does.
Ultimately, the goal is to treat your sweater vest like a playground. How well this works for you depends on how much fun you have with it. “Wow, a sweater vest,” your friends will say, a little confused. “A sweater vest,” you’ll reply. Then you’ll adjust your neckline, swing those unencumbered arms in the breeze, head back into the bar, and prepare to be emulated, eventually.
Lead image: sweater vest ($820), turtleneck ($390), and hat ($350) by Marine Serre.
This story appears in the September 2021 issue of Esquire Magazine. Subscribe to Esquire Select.
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