RIP Hoodies, Silicon Valley Swagger Has Arrived

The infamous “tech bro” hoodie wardrobe is over.

Some of Big Tech’s most powerful and richest chief executive officers are now rocking a new Silicon Valley swagger.

Take Meta’s Mark Zuckerberg, who exemplified the hoodie and T-shirt look for years but lately has been seen in a mob chic gold chain and $1,000 sheepskin Overland Rancher jacket, as well as the Alexander McQueen dragonfly appliqué evening jacket he chose as one of his looks for the weekend-long pre-wedding party of billionaire heir Anant Ambani and Radhika Merchant in early March.

Apparel choices typically come down to form or function, but for tech’s onetime boy wonder, this fashion renaissance may signal something more. Zuckerberg was 20 years old when he cofounded The Facebook in 2004. Now the Meta CEO is approaching 40 as one of the world’s most influential tech executives herding followers on multiple widely used platforms, including Facebook and Instagram, which have given him an estimated net worth of more than $152 billion.

That he would develop a taste for finer goods is not surprising, given how tech companies are expanding even more aggressively into the fashion world to grow their businesses.

The quiet luxury trend was a hit in tech’s C-suite before it made it to “Succession”‘s Kendall Roy. Last year, Loro Piana, the LVMH Moët Hennessy Louis Vuitton-owned purveyor of cashmere and vicunña that comes from Andean vicuñas, opened a store in Palo Alto with a limited collection backed by the Aura Blockchain Consortium.

But lately, tech leaders have been opting for more flash — and fashion with a capital “F.”

Technology and fashion, which have never been tighter in business, are coming together in the wardrobes of tech’s movers and shakers. The looks run the gamut across executives from Zuckerberg to Microsoft’s Satya Nadella to Tesla, X, SpaceX and Neuralink’s Elon Musk, showcasing their individual flair with designer goods or statement pieces on stages, in interviews and in their personal lives.

“It’s a matter of personal evolution and an organic shift that comes with maturing in the public eye,” said Michelle T. Sterling, personal stylist to technology CEOs and Global Image Group’s founder.

Bay Area retailer Sherri McMullen has also seen the tech contingent leveling up their style game firsthand.

“Many of our tech clients are interested in discovering new designers and investing in pieces that will take them from their daily activities to conferences they are speaking at, to the boardrooms they are leading,” said McMullen, the proprietor of McMullen boutique in Oakland, which stocks vibrant women’s clothes by Christopher John Rogers, Dries Van Noten and Stella Jean alongside quieter ones by The Row and Khaite. “This shift might be indicative of a cultural trend towards valuing personal style and presentation, even within the traditional tech-focused industries,” she suggested.

According to McMullen, there’s also a growing demand for fashion advice. “We have seen more of our clients interested in personal styling services and events that offer an opportunity to meet with other business professionals,” she said. “[So] we are hosting a series of conversations and dinners geared toward connecting people within fashion, art and technology.”

In March, McMullen hosted a dinner with CFDA award-winning designer Rachel Scott that had executives from Meta, Pinecone and other firms wearing her daring Diotima crochet knit styles.

“I’m still in my own exploration of ‘who am I’ in this world of people who don’t look like me,” said Kristen Werner, head of data at Pinecone, which is building search database technology to power AI, at the event dressed in a Diotima jacket with a peekaboo cotton crochet midsection. “Even women on my team, I’m like, ‘you can do it, don’t be shy, I got your back, nothing bad will happen to you, come sit at the table,’” she said of encouraging more creativity and spontaneity in dressing in tech.

Once upon a time, Silicon Valley seemed above the whims of fashion.

Apple’s Steve Jobs famously made a uniform of black Issey Miyake turtlenecks so he could free his mind to Think Different. Disgraced Theranos founder Elizabeth Holmes calculated her image of a black turtleneck and red lip to evoke Jobs — and prove she could hang in the too-often all-boys club.

But flashier personalities have dominated the headlines in recent months, like rocket man Elon Musk.

Musk’s “go f–k yourselves” look — made famous when he addressed X advertisers at a New York Times’ Dealbook Summit session in November — featured a $1,695 Belstaff mustang bomber jacket and dog tags.

The effect of the bomber jacket gave Musk, a billionaire many times over with a net worth of $197.7 billion, a rebellious “Top Gun” vibe that’s in line with his apparent ego and off-the-cuff personality. But when he does dress up, he reportedly has a fondness for Givenchy suits.

As masters of a rapidly expanding tech universe, he and others have seen their profiles raised with increasing visibility on Hollywood red carpets, in pop culture and on social media. Some understood early on how to maintain an image in the public eye. For others, it’s taken a little longer. But they’re coming around, and the fashion choices are rather revealing.

Zuckerberg has worn his swaggering Overland jacket everywhere from a Japanese McDonald’s to California’s Yosemite National Park. In March, the sheepskin-loving Meta CEO and Nvidia honcho Jensen Huang even switched outerwear for a fashion-swap social media post, like a couple of conspiring teens.

At this point, Nvidia’s Huang, who is worth $72.5 billion, is as famous for his black leather jackets as his company’s artificial intelligence tech. Whether collared or collarless, sleek or covered in zippers, he’s rarely been seen without one, and is so closely identified with the style that online purveyors sell affordable knock-offs with names like “Jensen Huang leather jackets.”

His latest favorite, a $9,000 Tom Ford lizard embossed biker jacket, is etched in the tech industry’s consciousness — largely because photos from Nvidia’s March press event have been everywhere. Flexing his company’s market position and strength in AI, the black leather jacket acts like a rebel yell on stage, although that could be fleeting. (Over the past few weeks, Nvidia’s stock has been up and down, at one point suffering a dramatic 10 percent drop, as AI momentum shifts in the investment scene.)

AI is clearly the wild frontier for tech and fashion. At a Google AI hackathon in March, Patrik Patrique Monique Arnesson, a Swedish football tech executive who goes by the moniker Princess Momo, caused a stir by wearing Jean Paul Gaultier’s “naked woman” bodysuit, which is something one would more expect to see on a Kardashian.

Google cofounder Sergey Brin, with disheveled hair and $2,600 Elder Statesman Wonderland checkered jacket, who was fielding a question from Arnesson during a question and answer session, carried on unfazed. But video of the nearly naked look broke the Silicon Valley internet, racking up more than 9 million views to date. Arnesson definitely made a point.

Microsoft CEO Satya Nadella spends at least some of his fortune, valued at some $1.35 billion, on premium footwear ranging from handmade shoes from Italy’s Scarosso at nearly $400 each to Lanvin’s $600 low-top sneakers. Google’s Sundar Pichai, whose fortune is estimated at $1.66 billion, favors Lanvin as well. He often pairs the footwear with a casual track jacket.

Apple’s current CEO, Tim Cook, leans more low-key. At Apple’s October 2023 press event, his meme-worthy choice of Black Nike Air Force 1s set off numerous online searches for the product. (He’s on the Nike board.)

At the 2024 Oscars, where Apple TV-Plus nabbed 13 nominations for films like “Killers of the Flower Moon” and “Napoleon” but didn’t bring home any statuettes, the Apple boss wore an unidentified tuxedo with a classic look that earned high marks from menswear pundits.

Reading tech’s fashion codes, Global Image Group’s Sterling believes that the “personal style development among the tech elite often mirrors the maturity of their brands and personal identities.”

For instance, she notices that Zuckerberg’s style has evolved naturally with age, but his penchant for blues and grays also lines up with Facebook branding. Huang cuts a bold figure in black leather, which matches the dynamic fields that Nvidia involves itself in, such as gaming, cryptocurrency mining and AI. Nadella’s business-casual look reveals an allegiance to tradition befitting Microsoft’s corporate ethos.

In other words, there’s deeper context in how tech execs present themselves. It speaks volumes about their mindsets, the ebb and flow of their fortunes, other challenging moments (testifying on Capitol Hill or, in Sam Bankman Fried’s case, in court) and life changes, from marriage to divorce, parenthood to even a new physique.

No one exhibits this transformation greater than Amazon mogul Jeff Bezos. With a net worth of nearly $196.4 billion, he is the poster child for those who have gone from weed-thin entrepreneur to bulked-up beefcake who can afford to style himself in any way he sees fit — and he certainly has been.

Since his divorce in 2019 and departure from the Amazon CEO role in 2021, he’s been cranking up the fashion volume louder than ever. Bezos has been spotted in everything from a space cowboy get-up to a tight-fitting boogie-printed shirt, complete with heart-shaped sunglasses for a costume party.

For the red carpet, he’s been known to coordinate with fiancé Lauren Sanchez’s outfits. And he’s a fan of extreme tailoring that shows off his physique, like the Laura Basci custom charcoal gray suit he wore to the Chanel x Charles Finch pre-Oscars dinner.

While Bezos’ style transformation didn’t take place until after he met Sanchez, the reality is that he has been focusing on fashion for years as part of his business, through Amazon Fashion.

Even in the post-Bezos era, fashion remains a high priority for the company. Although it couldn’t keep its ill-fated brick-and-mortar clothing stores alive, Amazon has seen a growing number of luxury brands entering the marketplace. Meanwhile, its developers continue to release new features for apparel shoppers — like the latest AI tools to help shoppers find the right fit.

The fashion imperative also goes beyond Amazon. Executives at Google, YouTube, Snap, Instagram, TikTok and other platforms all describe fashion as a critical focus. In fact, tech companies have been courting designers, brands and retailers for years now to extend their online advertising, boost their creator economies or integrate their AI and machine learning capabilities.

Snapchat expanded its augmented reality technology to accessories with more realistic visuals. Google followed up its 2023 AI apparel try-on by giving apparel shoppers a way to teach the search engine what they like based on its enormous Shopping Graph dataset. YouTube reckons that its creator updates will give brands a valuable way to test approaches and learn what works.

TikTok’s eagerness to align itself with important cultural moments has it set to sponsor the Met Gala next week — even as the U.S. Congress has passed a bill to potentially ban the social media platform unless parent Bytedance sells it. The Met Gala effort, according to the announcement, “will give our vast, global community insights into what we know will be a memorable and spectacular exhibition.”

TikTok follows in the footsteps of Instagram, which sponsored the event in previous years, crowning Adam Mosseri, head of Instagram, as honorary cochair in 2021 and 2022. Typically a low-key dresser, Mosseri stepped out that first year in a yellow and white graphic suit by New York brand Bode. In contrast, the ever-outspoken Musk attended the year after in a classic tuxedo with tails, with his fashion model mom Maye Musk as his date.

This interplay between tech and fashion isn’t limited to clothes, either. Tech has a habit of recruiting from fashion’s ranks.

Eva Chen was a fashion and beauty writer and editor before coming to Instagram. As Meta’s vice president of fashion and Instagram’s director of fashion partnerships, she has been instrumental as the platform’s ambassador to the fashion industry. Sally Singer also came from fashion journalism, running editorial and digital teams at Vogue before becoming Amazon’s head of fashion direction. One of the most famous examples is Angela Ahrendts, the former Burberry CEO who joined Apple to run its retail efforts in 2014. During her five-year term, Ahrendts shifted sales toward online ordering and focused the stores on human connection.

Lately, it seems the momentum is going the other way. Take Nike, for instance, which recruited Amazon’s Muge Erdirik Dogan and made her its new chief technology officer in November.

Silicon Valley and fashion may have seemed like strange bedfellows once, but no more. With all of their companies’ activity, it’s only logical that some tech executives realized style can mean good business and how they present themselves to the outside world can impact their net worth. It’s the culmination of a style journey that, for both titans and companies, took years and years.

The difference is that now industry leaders are not just talking the fashion talk, they’re walking the walk — and in some pretty fabulous shoes at that.

— With contributions from Booth Moore