From hoodies to tailored suits: how the wardrobes of tech billionaires have grown with their wealth

In April, he “subtly” expressed that he was in his necklace era while sharing about the release of the new version of Meta AI. He also sported much longer, curly hair, which he would continue to grow.

Come September, he would share on the Acquired podcast that he “started working on this series of shirts with some of my favourite classical sayings on them”. Printed on oversized t-shirts, these sayings include the Greek phrase “pathei mathos” (“learning through suffering” in English) and “aut Zuck, aut nihil”, a play on the Latin phrase “aut Caesar, aut nihil” (“either a Caesar or nothing”). 

Zuckerberg would also often pair them with a gold chain a la Eminem. His everyday neck candy is a design he worked on with New York jeweller Eli Halili to engrave the Jewish prayer he sings to his daughters every night, Mi Shebeirach.

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As Amazon grew to become one of the largest technology firms in the world over the past three decades, Jeff Bezos’ style evolved along with it. Bezos has gone from boring librarian to cool space cowboy, with style moments worthy of a Met Gala invite. 

In the early days of Amazon as a bookseller, Bezos would often wear a typical corporate outfit: a blue or white dress shirt and a pair of khaki pants. Occasionally, he would pair it with a dark-coloured blazer or sweater. 

As a 1999 Wired profile of Bezos put it, “For the kind of shopper Bezos represents, utility is, of course, a mantra.”

The same profile also detailed that he would buy shirts with hidden snaps under the collar point so that ties could be removed easily as well as multiple pairs of his favourite shoes to wear on rotation. 

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As Amazon ventured beyond books and into a wide range of product categories, Bezos swapped out his khakis for blue jeans and boots. Since then, his love for jeans has only expanded—from the denim-on-denim look he sported while announcing his rocket company Blue Origin’s lunar lander in 2019 to the distressed jeans he wore at Coachella last year.

Around 2017, when Bezos became one of the wealthiest men in the world, he started opting for a leather jacket over a business blazer. That year, he also turned heads with a polo and puffer vest ensemble at the Allen and Company Sun Valley conference.

In 2021, Bezos showed off another look: space cowboy chic. At Bezos’ rocket company Blue Origin’s first human spaceflight event in its New Shepard vehicle, the billionaire paired his flight suit with a cowboy hat and boots. This can be seen as an ode to his roots, having been born in Albuquerque, New Mexico, where the traditions of the Wild West era live on.

These days, Bezos goes between tailored suits in various neutral colours and the tech bro look that Zuckerberg has left behind. Occasionally, he trades them for a sleek tuxedo like he did for his Met Gala debut with fiancé Lauren Sánchez this year.

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Like Bezos, Elon Musk’s style evolution went from corporate casual to donning leather jackets and the occasional tux. 

His fashion sense started to transition in the early 2010s, after he founded several companies including software company Zip2, which he and his brother Kimbal sold in 1999 for US$307 million; fintech company PayPal, which was sold to eBay in 2022 for US$1.5 billion; and rocket company SpaceX, which is purportedly valued at around US$255 billion.

Since 2008, he has also been the CEO of electric car manufacturer Tesla, now the eighth most valuable company in the world with a market cap of US$1.107 trillion, according to CompaniesMarketCap.

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However, more talked about than his style is his hair transformation over the years.

When Musk first emerged on the tech scene in the ’90s, he had male pattern hair loss. But while Bezos chose to shave off the rest of his healthy hair, Musk’s hair grew fuller over the past three decades. Many speculate that he had a hair transplant, which he has neither confirmed nor denied.

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Musk became noticed by the fashion set in 2018 when he made his virgin Met Gala appearance alongside Canadian singer and then-partner Grimes, with who he has three children. To the fashion event of the year, he wore a white tux jacket with text on the back that read “novus ordo seclorum” (“a new succession of ages” in English).

It was a solid attempt by the pro-Trump techno-libertarian, if only people could see the words. As Grimes said in an interview with Vanity Fair, “His shirt says something cool, but you can’t actually see it because it is so white that it like disappears.”

When Musk attended the 2022 gala with his model-dietician mother Maye, he shared with reporters his love for fashion: “Sometimes [fashion] is viewed as frivolous and not that important, but I think beauty is very important and style and things that move the heart.”

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This year, he has been actively expressing his political views through his outfits, pairing his usual graphic t-shirt, blazer, cowboy belt and pants get-up with the Maga (Make America Great Again) cap. He has the headgear not only in its trademark red colour but in gold and black, too. He also has the cap with text embroidered in a traditional blackletter font, which he pointed to during a campaign rally for incoming US president Donald Trump and said, “I’m dark gothic Maga”.

We’re looking forward to seeing Musk’s style evolve further as he adds “politician” to his title and leads the Trump administration’s new Department of Government Efficiency (DOGE).

Read more: What JPMorgan Chase’s Jamie Dimon thinks about the economy, frenzied young people and Trump

Jack Dorsey, the co-founder of Twitter, was once called the most stylish guy in tech in 2015 by GQ magazine for his penchant for dark, slim suits in a sea of tech bro fits.

He originally wanted to become a fashion designer and admired the work of jeanmaker Scott Morrison, the founder of New York jeans brand Paper Denim and Cloth.

According to American journalist and author Nick Bilton’s 2013 book, Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal, Dorsey also reportedly told one of his Twitter co-founders Noah Glass about his “exit strategy” a month before the social media platform launched in March 2006. He said, “I’m going to quit tech and become a fashion designer.”

He continued to pursue his fashion design dreams during his early days as Twitter CEO, taking classes at the design school, Apparel Arts, in San Francisco.

His style, however, wasn’t always about well-tailored suits.

Read more: Asia’s top fashion designers have made a profound impact on global style

In a 2013 interview with CBS’ 60 Minutes, Dorsey revealed that he raised Twitter’s first round of fundraising with dreadlocks and a nose ring.

A few years into founding Twitter, he experimented with the Wall Street preppy style (sweater or blazer over a shirt), perhaps to fit investors’ expectations of what a burgeoning tech startup founder should look like at the time.

As Twitter established itself as one of the leading social media companies in the world, Dorsey’s look stayed polished but decidedly more tech-bro casual. He continued to style his hair neatly, while also growing it and his beard out.

In 2018, Dorsey’s nose ring made a comeback after years on hiatus. Given the reception its re-appearance got, one would think it was the comeback of a popular K-pop band. Quartz reported on the day of the reveal that Wall Street embraced Dorsey’s nose ring, as stock prices for both Twitter and Square—another company he founded, now called Block—increased. Dorsey, however, said it was simply a coincidence.

Not causal. @nedsegal

— jack (@jack) June 8, 2018

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Dorsey wearing an oversized black beanie was probably one of his most viral looks. The outfit that the entrepreneur wore to Ted 2019 in Vancouver made him a meme on his own platform, with one Twitter user saying, “Is it just me or does Twitter CEO Jack Dorsey look like he just got back from a Game of Thrones’ shoot?”

Less jokingly, women also called out his onstage beanie-hoodie ensemble as a double standard. One Twitter user wrote: “FUN CHALLENGE: every single professional woman show up to work dressed like this”. The post has since received more than 13,000 likes and over 300 comments, the majority from other women.

FUN CHALLENGE: every single professional woman show up to work dressed like this pic.twitter.com/ffPh8cQz9n

— Ariel Dumas (@ArielDumas) April 17, 2019

Towards the end of his tenure as Twitter CEO, Dorsey had another iconic fashion moment—this time at the Bitcoin Convention in 2021 in Miami, Florida. Dorsey appeared in an orange-yellow tie-dye t-shirt that match perfectly with the cryptocurrency’s logo featured on the screen behind him as he spoke on stage. He also sported a buzzcut, a longer beard and a healthy tan.

The next year, the entrepreneur stepped down from Twitter’s board and the company was sold to Musk for US$44 billion.

These days, it’s harder to catch a glimpse of Dorsey’s style preferences, as he quit Instagram in 2023. In the public appearances he has made, like the Roc Nation Sports Super Bowl Party this past February, he was back to black and best expressing himself in his signature ensemble of hoodie sweatshirt and slacks.

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