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Cool or Tool?: Vests

Warning: When you bid farewell to arms, you may open yourself up to attack

The stand-alone vest—favored by Justin Timberlake, Cedric the Entertainer, and circus ringmasters everywhere—is a little bit like that eccentric uncle you see only at Thanksgiving: occasionally endearing, mostly mortifying, and always better in small doses. Liberated from the three-piece suit, the vest can assume remarkable powers, like the ability to turn otherwise anemic inhabitants into the kind of guys who attract Kate Moss. But more often than not, the magic works in reverse, and suddenly you're a balding high-school art teacher with a ponytail and a kiln full of shattered dreams. If you're already comfortable in a V-neck T-shirt and skinny jeans—or an ascot and double-breasted tweed—donning a vest can be relatively painless. One false step, though, and even the dandiest Oscar Wilde can find himself undone by the powder keg strapped to his back, leaving behind the charred, cartoonish shell of Bill the Butcher from Gangs of New York. Wear it too short, especially with a ripped tee hanging out, and you're ready to audition for a Chelsea boy band; wear it tight like a corset and you're Keira Knightley's chambermaid, or worse, Luther Vandross: The Chunky Years. Leather is out of the question. And forget about embellishments like chains, scarves, or appliqués. In other words, you're going to need to make a real commitment to get it right. If it's any reassurance, Dsquared designer Dan Caten remains solidly pro-vest, despite all the perils. "When worn correctly, a vest can hide a multitude of sins," he says. "They're like skirts for men."

Photograph courtesy of WireImage.com

COOL: Penn Badgely

Photo: Bauer-Griffin.com
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