Not since the Seventies have leather jackets been so prevalent in men's style. And you don't have to be Joey Ramone to pull one off. Look for one that is already distressed, so it seems like you've had it for years, and then pair it with something to soften the edges, like a dotted scarf or a sweater. It will still look badass – but relaxed. "A leather jacket isn't something you can just buy online," Wooster says. "You have to go out and try them on until you find the one that works for you. The jacket should be snug but not tight. You'll just know it when you've found the right one." [Hugo Boss Josol Jacket, $418; us.hugoboss.com]
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