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Silicon Valley’s Tech Elite Are Rocking a Stylish New Look—Here’s How to Master It

Bezos and Zukerberg are ditching the scruffy hoodies and ill-fitting jeans in favor of Loro Piana cashmere and Brunello Cucinelli sneakers. You should too.

Jeff Bezos Photo: Getty Images for WIRED25

If you’ve bumped into Jeff Bezos lately, you’ve probably noticed his wardrobe one-eighty. Once a rumpled nerd in baggy chinos, these days the Amazon billionaire can pull off a fine suit as well as any fastidious investment banker. Tailored to frame the biceps just so, bold with a cutaway collar and a slick Windsor knot at the throat, his look exudes power, wealth, and a meticulous attention to image that his old Gap-wearing self wouldn’t recognize.

It’s all part of a wider sartorial shift that’s happening in Silicon Valley. Tech execs are trading in their dorm-room duds—you know the look: hoodies, gray Ts, disheveled jeans—for fine fabrics, custom tailoring, and sharper fits. What prompted the change in style? Perhaps they simply grew up and learned to appreciate quality materials. Or maybe it’s because luxury brands like Brunello Cucinelli and Kiton have noted that those Silicon boys are sharpening up,
and have tailored their offerings accordingly.

Kiton’s CEO, Antonio De Matteis, answers their prayers with softly structured, lightweight cashmere and 40-micron wool jackets with natural stretch. “These are guys who are precise in what they want,” he explains. “They want less structured jackets and trousers that fit and feel like a favorite pair of jeans. But they still want crisp white shirts, and lately they have been buying a lot of neckties.”

Curiously, tech’s fascination with luxury fashion has made Brunello Cucinelli himself a man about town in Silicon Valley. He has been the surprising force behind some of the industry’s most iconic looks from the past: His was the label inside Steve Jobs’s signature black turtlenecks, which he delivered in custom batches, and he does the same thing with Mark Zuckerberg’s custom gray T-shirts. Bezos’s new look, which is heavy on ultra-soft cashmere jackets
and luxurious leathers, is also largely owed to the designer. And in this industry, when the titans gaze upon you with favor, you quickly reach rock-star status: Cucinelli has been invited to speak at Dreamforce—the annual Salesforce motivational conference—twice (!) and in 2017 took the stage for an event billed as a fireside chat with Salesforce founder Marc Benioff, who wore a pinstriped navy suit made of rare vicuña (one guess as to whose name was on that label).

Pinstripes aside, Silicon Valley’s new look is largely a pared-down version of the old Wall Street style, says Bob Mitchell, copresident of Mitchells stores, which owns Wilkes Bashford in San Francisco and Palo Alto. The Zegna ties and dark suits common to the East Coast are overly formal for
the Silicon Valley set, leading brands to mellow out their looks in response. Kiton and Loro Piana have gone the way of Cucinelli’s “sportivo chic,” releasing more casual—but
no less refined—sport jackets and sweaters. Sneakers have also exploded—just not in
an athletic sense, obviously. Instead, the luxe-leather look has become almost the de facto staple thanks to Lanvin, Cucinelli, and Loro Piana’s sophisticated options.

The money-making potential of this new attention to fashion can’t be understated. Mitchell says his strongest growth markets are in Seattle (where Amazon is based) and Palo Alto. And ironically, 97 percent of his sales are in-store rather than online. “The tech person actually appreciates personalized service,” he says.

So have the sloppy geeks
all but gone extinct? Not quite. Though venture capitalist Jason Mendelson, a former software engineer and cofounder
of Colorado’s Foundry Group, wouldn’t be caught dead in a hoodie, he’s not one who has been buying those ties, either. Instead, he rotates through a collection of Eton shirts, which conveniently come in three barrel sizes. “I have no tolerance for shirts that don’t fit,” he says.

And then you have the worker bees clogging the cubicles of the latest start-ups, most of whom still faithfully channel Zuckerberg’s shabby Social Network look to a T (literally). You can’t blame them. He practically invented the notion that the smartest guy in the room doesn’t have to dress well—he’s going to change the world! But back in 2012, the social-media kingpin nearly walked away from a round of Wall Street meetings empty-handed,
and it was all due to his trademark navy-blue hoodie. Investment bankers and analysts were downright insulted. Was his lazy apparel a sign of disrespect or a manifestation of the future? The hoodie became so notorious, it even landed its own Twitter account, @ZuckerbergsHood. Its bio reads, “I got Mark’s back. Behind every great billionaire is a really great hoodie.”

News flash: not anymore.

Silicon Valley Wardrobe Staples

The modern-day techie’s essentials are more than meets the eye. These not-so basics—in cashmere, leather, and suede—come from the biggest names in men’s fashion.

Silicon Valley Wardrobe Staples

Silicon Valley Wardrobe Staples.  Photo: Michells

Loro Piana

Sure, Zuckerberg may have started out wearing $20 polyester hoodies, but he—and the legion of unicorn CEO’s he’s inspired—have graduated to the big leagues. Today, they’ve swapped synthetic fabrics for the finest stuff on the planet: namely, Loro Piana’s super-soft cotton-and-cashmere blend. There’s no mistaking the brand’s hoodie shown above on the right ($2,195) for anything less than exquisite.

Lanvin

Lanvin’s sneakers ($490, on the bottom right) may look like the converse you wore through college, but with fabrications like wool-and-felt or leather-and-suede and chic monochrome colorway makes them boardroom ready. Pair them with your favorite worn-in jeans for the laid-back Silicon Valley look, or use them to keep a suit from looking overly stuffy.

Kiton

Kiton was one of the first brands to loosen its buttoned-up aesthetic to appeal to tech royalty. Its blazers that are easy to throw on in place of that ubiquitous hoodie, like the navy-and-green cashmere style shown above on the left ($7,595, available at Kiton boutiques nationwide), are a go-to for meetings with VC fund managers.

Brunello Cucinelli

Like Kiton, Brunello Cucinelli was one of the first brands to tap into the Silicon Valley cash cow. The Italian brand’s dressed-down staples, like these suede-and-leather sneakers ($995, top right) are mainstays in wardrobes of CEOs across the Bay Area thanks to their polished—but always casual—feel.

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