The contemporary style codes of Silicon Valley are best illustrated by two Sams. At one extreme there is Sam Bankman-Fried, founder of the now-bankrupt crypto exchange FTX whose stunning fall from grace may have been portended all along by his spectacularly bad taste in clothes. At the other end of the spectrum is Sam Altman, the 38-year-old chief executive of OpenAI, the startup behind ChatGPT (maybe you’ve heard of it?), which Microsoft has deemed so valuable it has cut a $10 billion deal.
As de facto leader of the artificial intelligence revolution, Altman presents himself as an avatar of good ethics and social responsibility, reinforcing this image with a wardrobe of refined, very expensive-looking knitwear. Was that a Loro Piana baby cashmere crewneck he was seen sporting recently? We’ll never know for sure—and isn’t that the point? It was definitely the point for the captains of industry of an earlier generation, whose C-suite closets put a premium on fabrics, not flash, on “pinstripes in the p.m.,” as Lisa Birnbach put it, not on gray tees and jeans like Mark Zuckerberg or the 24-7 peacocking of the cryptocracy. Discretion, they knew, is the better part of valor—and clothing. Their modern-day counterparts may have once eschewed formalwear, but it seems there’s been a disturbance in the force of late.
Even before Silicon Valley Bank’s collapse in March brought fresh scrutiny of tech overlords and their spending, stealth power dressing was taking root in Palo Alto. That same week Loro Piana, the century-old stalwart of sotto voce eleganza, opened a new boutique in the town. “We thought this would be a market that could be very interesting for us,” says Matthieu Garnier, the brand’s North America ceo.
And for some recent court appearances Zuckerberg traded his signature hoodies for sharp tailoring. In fact, it was the Meta boss who seemed to be on the mood board for embattled TikTok chief Shou Zi Chew as he went on a charm offensive this spring on Capitol Hill. In his natty navy suit and tie, he sought to reassure anxious lawmakers by adopting the uniform of a boring congressional aide.
“They are masters of their domain, of the universe, but when it comes to clothing they just want to fit in,” says Josh Peskowitz, a former menswear buyer who is now an operating partner at Untitled Group, an investment firm that focuses on the luxury sector. “What I have always found interesting about these quote-unquote titans is that most of them just want to dress so that nobody will make fun of them.”
Which is not to say they don’t care about the semiotics of style. They have a keen understanding of the power of iconography. Exhibit A: Steve Jobs’s black Issey Miyake mock turtlenecks remain a go-to signifier for aspiring founders, for better or worse (see: Elizabeth Holmes).
And let us not forget the army of image consultants and stylists this cadre quietly keeps on retainer. According to a house manager who has worked for some of Silicon Valley’s biggest names over the past two decades, a number of them employ the services of A-list Hollywood stylist Karla Welch, who is more famous for clients like Justin Bieber. (We asked Welch to comment, but she seems to have adopted the low profile of her clients.) “They play it down,” the manager tells T&C. “They don’t want anyone to know that they’re actually focusing on looking nicer. And yet they’re using someone who dresses movie stars.”
There is no denying, however, that these boy geniuses have grown up. And if they appear to have successfully rehabbed their sense of style into a kind of old-money-esque expression of #IYKYK luxury, that may be nothing more than a natural evolution of their core values. Practicality has always been the driving MO, and what’s more practical than a Gap T-shirt? A Brunello Cucinelli T-shirt that lasts forever.
“The mentality of the tech entrepreneur has not changed, which is that he doesn’t want to think about his clothing,” Peskowitz adds. “But wearing pajama pants and Allbirds is unacceptable.” The growing demands of the job, for one, make this so. As does adulting in general.
Zuckerberg now requires a versatile wardrobe that can take him from an investor meeting to his kid’s soccer game, from a Senate hearing to a wedding on the Amalfi Coast, from a backyard BBQ to Sun Valley. “The subtle nuances are out there, and they have to permeate after 10, 15, 20 years as you grow, your needs expand, and your environment changes,” says Victoria Cardenas Hitchcock, an imagemaker who has been revamping the closets of tech executives at places like Meta, Apple, and Google since the ’90s. “And don’t write off the fact that it’s quality. It looks good.”
Succession’s resident tech bro Lukas Matsson (Alexander Skarsgård), definitely a low-key rich nerd.
Brunello, Zegna, Kiton, and Loro Piana have been the hushed status symbols of the San Francisco rich for ages. Much of that has to do with the Bay Area lifestyle: more hiking and outdoor activity, less theater and late night dining. “It’s a sweater city, so cashmere is our number one fiber,” says Emily Holt, the owner of the Marin County boutique Hero Shop. “And it’s a city where there is also a lot of style shaming. There has always been a more relaxed, casual, under-the-radar vibe in terms of luxury dressing.”
Therein lies the irony. As much as this is a town of disruptors and unicorns and radical problem solvers, conformity is still de rigueur. They have come to realize that standing out, at least sartorially, invites raised eyebrows or, worse, ridicule. Google “Jeff Bezos, New Year’s Eve 2021.”
In other words, they’re still nerds at heart. “These guys work in tech,” Holt says. “It’s not their job to have any idea of the codes of fashion. Silicon Valley is not New York.”
This story appears in the May 2023 issue of Town & Country. SUBSCRIBE NOW
Leena Kim is an editor at Town & Country, where she covers travel, jewelry, education, weddings, and culture.
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