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Billionaires Dressing Badly: The Silicon Valley Style Crisis

The tech world has grown up a lot. So why do its biggest stars insist on dressing like slovenly teenagers?

DECEMBER 2012 / Tuesday, January 01, 2013

At the annual Macworld and CES conferences in January, a parade of visionary executives will take to the stage to tout their amazing new products. And yet it seems that to show off tech tools, you have to dress like one. These entrepreneurs will look more like college students on laundry day than the titans they are. They'll wear ill-fitting jeans and shapeless button-downs. Sure to be present in abundance: the hoodie, most famously associated with Facebook's Mark Zuckerberg ("I never take off the hoodie," he's bragged in interviews) but also favored by Twitter's Biz Stone, Tumblr's David Karp (right), and other next-gen moguls.

Silicon Valley, it's time for an upgrade. Yes, casual dressing is endemic to Northern California. "The only people who really wear suits are waiters and people in retail," says New York City-based menswear designer Patrik Ervell, who grew up in the Bay Area. And that's especially true in the Valley and other tech hubs, where dressing like you don't care is part of the community's anticorporate ethos. But there's a difference between studied nonchalance and studied noneffort. At least Steve Jobs' iconic uniform (black turtleneck, stonewashed 501s, gray New Balances) showed a certain rigor—his look said he was too busy creating revolutionary products to bother with a tie. "The way Jobs dressed was super-iconic," Ervell says. "But someone like Mark Zuckerberg just looks juvenile."

And the idea of a kid running a multibillion-dollar company doesn't inspire confidence. One analyst described Zuckerberg's choice to meet investors last spring before Facebook's IPO dressed in his usual dorm-style outfit as a "mark of immaturity." Indeed, it no longer makes sense for tech execs to look like they've just emerged from an all-night coding session. With technology occupying such a central role in our lives, some savvy figures in the industry are recognizing this: Napster cofounder and former Facebook president Sean Parker, once the dot-com world's enfant terrible, now favors Italian suits as he doles out venture capital.

At a certain point, disregard for the Man's sartorial code starts to feel like disregard for us. One aim of dressing smartly has always been to show respect for those you meet—and looking like a slob while extolling the virtues of your new wonder product suggests you don't give a damn if we buy what you're selling.

Evan Williams, Twitter.

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