Mark Zuckerberg has been labelled many things — a privacy apathetic CEO for some years and a feature cloning expert — but when it comes to fashion, he is somewhat the James Bond of the tech world. You can almost hear him say “I know a good tailor in Silicon Valley,” trying to be Sean Connery in Diamonds Are Forever.

Recently he had an announcement around AI, which most may have forgotten, but somehow the image of him wearing a chain necklace is making me drop down on my knee, looking skywards for a shower of moolah to purchase one of those chunky charms, even if it brings on ASAP Rocky vibes on a man two sizes bigger than Mr T.

He had that entire 1990s Miami vibes, almost to the point of getting a role in Full House, giving John Stamos’ Uncle Jesse some stiff competition. The celebrity Instagram account The Shade Room even put out a doctored version of the chain-chain picture in which Zuck sports some facial hair, receiving a nod from the man himself.

However Meta fares — even if its Reality Labs, the company’s hardware division, loses a few more billion dollars over the next few years — Zuckerberg is ensuring the fashion playbook of Silicon Valley is not boring. He is not alone. Amazon man Jeff Bezos and X man-boy Elon Musk too have some cool tricks in their wardrobes.

Loro Piana versus Buck Mason

Recently, Mr Z was in India for the blitz-glitz pre-wedding gala of Anant Ambani and Radhika Merchant. He almost stole everyone’s fashion thunder by slipping into a Rahul Mishra hand-embroidered number featuring a majestic tigress from the Sunderbans, prompting Microsoft co-founder Bill Gates to say: “You’ve always been great at dressing for the occasion.”

Mark Zuckerberg in a Rahul Mishra hand-embroidered number featuring a majestic tigress from the Sunderbans. It prompted Microsoft co-founder Bill Gates to say: “You’ve always been great at dressing for the occasion.”

But that was just a glimpse of what the man has been wearing recently. Consider the moment when he corrected the journalist Jen Wieczner of New York magazine when she wrote an article identifying a sweater Zuck wore as being from the brand Loro Piana. He didn’t hesitate to jump into the comments section of the magazine’s Instagram post to let the world know that it was actually a crew neck from Buck Mason, a Los Angeles brand that focuses on American classics.

It’s the same 39-year-old tech mogul who once made journalists run towards the keyboard to knock out a 1,000-word copy about how Zuck wears grey Brunello Cucinelli T-shirts all the time so as to save time while choosing his look every morning.

Loro Piana is one of those brands that you can’t recognise easily. OpenAI man Sam Altman could have been wearing it all the time but this a 100-year-old brand that doesn’t throw tags at you, instead it allows its cut and fall make the wearer proud as a peacock. Zuckerberg hasn’t turned his back on LP but he also experiments with other brands, like Buck Mason, Todd Snyder, and John Elliott for his shirts, sweaters, and pants, points out Wieczner. For his workout gear, beachwear and athleisure, a mention needs to be made of Vuori and Outerknown. On his feet are sneakers from Nike and slides from Adidas.

Sam Altman is taking the "tech bro" look to a new level.

Z’s generation of entrepreneurs require a versatile wardrobe, a concept far removed from the 1980s era of Silicon Valley. He has kids, so something to wear to the soccer game. Plenty of investors hang around him, so something to fit in that zone. From time to time, he has to go for Senate and Congress hearings, and for that something traditional works. When he is at a wedding, there is a more chilled vibe.

Be it the Meta chief or his peers, the likes of Loro Piana, Brunello, Zegna and Kiton remain hushed symbols of tech’s Mecca. They are meant for people who like to vibe to under-the-radar luxury dressing.

However Meta’s luck on Wall Street, its owner is always seen at his finest. We are seeing the touch of the finest tailors for his suits and he can pull off a shearling jacket like no other. He can even rock a ribbed cardigan (from John Elliott) that makes Instagram go into a tizzy. The $7,000 Alexander McQueen dragonfly embroidered blazer he wore to the pre-wedding festivities of Anant and Radhika did justice to his wife Priscilla Chan’s black Alexander McQueen evening dress featuring a hand-drawn gold embroidery with Colorado topaz stones and silver crystals applique handwork.

Muscled-up look of Bezos

Don’t mistake Zuckerberg’s middle-aged makeover as midlife crisis. Hoodies have become a cliche in San Francisco. Executives are trying to break the mould, opting for tailored looks. This goes against the careless wardrobe ethos that the tech industry has become synonymous with. The 1983 book The Official Silicon Valley Guy Handbook mentions that “Clothes make the man, everywhere but in Silicon Valley. Here almost everyone dresses alike, and not very tastefully at that.”

If Zuckerberg reflects the look of the middle-age Silicon Valley entrepreneur, Amazon boss Jeff Bezos is showing what it means to be fit at the age of 60.

His wardrobe is as much about tradition as it’s about giving young CEOs stiff competition. The man dresses to ensure the focus is on him, which goes with the image of a man who is at the helm of a tech empire that includes moviemaking. He has effortlessly moved from pleated pants to a muscled-up look. The removal of his mud-brown hair and the addition of bulge around the biceps have helped. Bring on that Garrett Leight Van Buren sunglasses and cowboy boots. BuzzFeed has described it as “Terminator-meets-Vin-Diesel- in-Portland”.

It’s the same man whose 1999 Wired profile said his wardrobe consists of white or blue dress shirts and a pair of khaki pants. “Back in the late ’80s in New York, when he had to wear a suit every day to the office, he gained a preference for shirts with hidden snaps under the collar points for easy tie removal. He has trouble locating this style in the Pacific Northwest, so now he buys a pack of standard snapless shirts and has the snaps sewn on.”

Lately, he has been less involved in the everyday functioning of Amazon and plays a more public role.

Dressing up for the occasion means something special because in a span of a few hours he could be meeting the political power crowd and then a bunch of tech geeks.

Dressing to get noticed

On the other end of the fashion spectrum is Nvidia CEO Jensen Huang. He has built a chip empire that’s now worth over $2 trillion. His look is not as fresh as that of Zuckerberg or Bezos but you can consider him the Bono of tech valley, a man who likes to wear black leather jackets that fit well.

Very little changes about his leather jackets — at times they have collars, at times a lot of zips and then there are those that look like motorcycle jackets. Of course, all of them are black.

It makes him recognisable but, at the same time, it’s the opposite of the swish set of Silicon Valley.

Nvidia CEO Jensen Huang's black leather jacket is gaining attention among both fashion and tech enthusiasts

His spokesperson told The New York Times: “He’s said before that he dresses in the same style of black pants and shirt because it presents one fewer set of decisions to be made each day.”

But it’s not that simple. In the 1950s, Hollywood turned the black leather jacket into something rebellious and a piece of clothing with sex appeal. Remember James Dean or Elvis Presley? It’s a calculated step the 61-year-old has taken because at his age khakis may not be the best option but a leather jacket can help put pedal to the metal during tech meetings.

The jackets worn by Elon Musk are worlds apart. At the New York Times DealBook conference, he tried to showcase masculinity in a leather flight jacket with a fur-lined collar.

Elon Musk speaks onstage during The New York Times Dealbook Summit 2023 at Jazz at Lincoln Centre on November 29, 2023 in New York City.

Using wardrobe to manage the occasion is something familiar with TikTok’s Singaporean CEO Shou Zi Chew. The social media platform is under tremendous political pressure in the US and is on the verge of getting banned or sold but Chew is keeping his cool by wearing clothes that spell diplomacy — blue suit-blue tie uniform. When the occasion demands, he moves to a simple (and not so simple) pair of jeans and T-shirt.

TikTok CEO Shou Chew and his blue suit has become a talking point

The Jobs look

Yet, one can’t forget a man who become the symbol of minimalistic fashion — Steve Jobs. He preferred $175 St. Croix cotton and microfibre mock black turtlenecks and bought about two dozen black turtlenecks each year.

Steve Jobs, in Paris On September 17, 1998

The turtleneck was inspired by the uniforms of factory workers in postwar Japan, and influenced by a high fashion designer. According to biographer Walter Isaacson: “He became friends with (Issey) Miyake and would visit him regularly. He also came to like the idea of having a uniform for himself, both because of its daily convenience (the rationale he claimed) and its ability to convey a signature style. ‘So I asked Issey to make me some of his black turtlenecks that I liked, and he made me like a hundred of them.’ Jobs noticed my surprise when he told this story, so he showed them stacked up in the closet. ‘That’s what I wear,’ he said. ‘I have enough to last for the rest of my life.’”

Also close to his heart was his Levi’s 501s and New Balance shoes. But it was the turtleneck that made the world’s most recognisable CEO to the point it got embedded in pop culture. The now disgraced Elizabeth Holmes of Theranos adopted it when she was trying to tell the world of her Jobs-like brilliance.

However, much the wardrobe changes in Silicon Valley, there will always be room to dress up like a tech bro, which involves a zip-up vest or gilet. It was a look popularised many years ago for the elite Allen & Company Sun Valley Conference in Idaho or the “summer camp for billionaires”. You really can’t go wrong sporting hoodies and sweatshirts by Loro Piana or Brunello Cucinelli, often with price tags that can be mind boggling. Add to that Lanvin sneakers Rick Owens jersey knits and bomber-style jackets.

Boring to bold, Silicon Valley bigwigs no longer shies away from getting wardrobe help from stylists like Victoria Hitchcock and Peter Nguyen. The era of AI is something new for the tech industry, and it brings with it a wardrobe switch up. They, of course, still want to fit into an image but at the same time appear well dressed, complete with five-pocket chinos and Zegna sweaters.

It’s no longer out of place to see Bezos turn up at a Dolce & Gabbana fashion show or Tim Cook at the Oscars. If Bezos can pull off a $1,000 Brunello Cucinelli jeans and a more than $1,200 Casablanca printed shirt, Cook looks like he is at home wearing a “beautifully tailored, well proportioned, no puckering or pulling” black tuxedo, as menswear writer Derek Guy puts it.

Apple CEO Tim Cook at the 96th Annual Oscars held at Ovation Hollywood on March 10 in Los Angeles

Silicon Valley is indeed having a Succession moment. The well-tailored suits that Kendall Roy wears on the HBO show prove the power of “stealth wealth” fashion where borders between brands go beyond brand tags. It’s the charm of not having a flashy or recognisable logos in sight. And that has always formed the heart of the Silicon Valley fashion play — a distaste for gaudiness. Sure, Zuckerberg’s new wardrobe is bold but it has a touch of the tech industry’s undeclared uniform — quiet luxury.