The Fashion Evolution of Tech Leaders: Breaking Stereotypes in Silicon Valley

Author Lia Andrienko
Category Lifestyle
Date July 16 2023
Reading Time 4 min.

The Fashion Evolution of Tech Leaders: Breaking Stereotypes in Silicon Valley

Today, we will delve into the world of Silicon Valley style. How do people who drive the success of the largest technology giants dress? Is there a distinct style that sets them apart from stereotypes?

You may not be interested in fashion, but ignoring it is impossible if you want to have a successful career in business. There is a difference between “not caring about fashion” and “not caring about oneself.” Visual appearance creates strong and lasting emotions that are remembered and stored in the minds of those around you. Each industry has its own dress code, just like it has its own hierarchy.

Photo: Chanel SS17 Photography Evan Schreiber

In the world of technology and startups, image formation also holds significance. Industry leaders understand that their outward appearance can enhance their business reputation.

Image formation is not just about appearance; it is also a way to connect with a specific community. Silicon Valley is known for its t-shirts, jeans, and sneakers.

The godfather of Silicon Valley style was Steve Jobs. His meticulously crafted image and style helped embed the idea of a brilliant founder in the minds of tech enthusiasts: minimalism and monotony bring additional productivity. The startup culture is solely based on how well you code, rather than presenting oneself as a personality.

Which brands do the well-known bosses of IT companies prefer? Many people believe that they disregard their appearance and clothing, while in reality, in the Valley, a completely different and rather expensive style has emerged, far from Zara, Bershka, and Pull&Bear.

The Guardian has dubbed Silicon Valley the new Hollywood, and its residents as the new stars that people want to emulate, including their fashion sense. “Free sushi, massage chairs, heated toilet seats—employees of leading companies live like celebrities,” says Ravi Belani, the director of Alchemist, a startup accelerator, and entrepreneurship lecturer at Stanford University. Troy Carter, the former manager of Lady Gaga and current venture capitalist in Silicon Valley, told Time magazine about the sensation he felt that the new glimmer from the glass offices of Silicon Valley did not go unnoticed by the fashion world.

The founders of technology companies are maturing; they are attending social parties and carrying themselves into the world of celebrities, bankers, and businessmen in brands like Saint Laurent, Christian Louboutin, Rick Owens, and more.

Let’s start with the founder of Facebook, Meta – Mark Zuckerberg. We’re accustomed to seeing him in gray t-shirts, but not everyone knows that they are actually customized from Brunello Cucinelli, and his cashmere hoodies come from the Italian brand Loro Piana. Zuckerberg also complements his look with Nike sneakers, specifically the Flyknit Lunar model in various shades of gray. This same model is sometimes worn by Elon Musk.


The founder of Snapchat, Evan Spiegel, is known for his impeccable style. In 2015, he even appeared in the pages of Italian Vogue. He wears shirts from Hackett London and James Perse, sneakers from Common Projects, and his wardrobe also includes bombers from Saint Laurent and white Common Projects sneakers with gold numbers.

Kevin Systrom, the founder of Instagram, is a fashion enthusiast in the IT industry. He enjoyed interacting with Karl Lagerfeld, and he is friends with the top management of Louis Vuitton, always keeping up with the brand’s latest offerings. Systrom is a fan of expensive Brioni suits and appreciates their soft tailoring.

Fashionable footwear in Silicon Valley is not particularly focused on local innovative sneakers made from eucalyptus and cellulose. Instead, people prefer brands like Yeezy, Loro Piana, and classic suede Lanvin sneakers, which are favored by Google CEO Sundar Pichai, Google co-founder Larry Page, Microsoft CEO Satya Nadella, and Instagram founder Kevin Systrom.

Airbnb CEO Brian Chesky prefers SeaVees sneakers priced at $60, but he also enjoys wearing luxury sneakers like Gucci.

Tim Cook, CEO of Apple and a board member of Nike, opts for Nike sneakers.

Twitter CEO Jack Dorsey chooses expensive and stylish items and is a fan of Rick Owens. He selects sneakers from the brand priced at $1000 and classic high-tops worth $1900. Dorsey’s all-black outfit can be replicated by any fan, with a $10 H&M t-shirt, $75 slim jeans from Topman, and $60 Calvin Klein Ibiza sneakers.

Susan Wojcicki, the CEO of YouTube, prefers New Balance sneakers.

Salesforce CEO Marc Benioff favors Christian Louboutin sneakers, featuring red lacquered toes, metallic inserts, and cloud appliques with prices starting from $1500.

Sam Altman, the president of Y Combinator, can be seen wearing the latest Yeezy sneakers, collectible Nike shoes, and Puma Blaze of Glory sneakers.

Silicon Valley, people wear brands like Rag & Bone, Y-3 accessories, custom-made Bode shirts using vintage fabrics, and bespoke footwear from Al’s Attire.

Photo: Thom Browne

The shift towards a more fashionable mindset has been driven by new business and social opportunities. Jeff Bezos, who launched Amazon from his garage, used to wear wide khaki pants and blue linen shirts. But now, there’s a different Jeff Bezos who can be seen in Cucinelli and Crime Scene Investigator t-shirts. He prefers a smart-casual style, with excellent leather jackets, straight jeans, and polo shirts in his wardrobe. When he opts for a more formal look, he chooses well-fitted suits and the right accessories. The new Bezos now interacts with Hollywood’s film and television elite as he expands his business into the media empire. Occasionally, Bezos is seen wearing Prada sandals, a Brunello Cucinelli jacket, or Kiton attire.

Even the cornerstone of Silicon Valley style, the vest, has undergone a fashionable update in recent years. Executives have transitioned to sleeveless down jackets from Moncler and Herno.

Elon Musk has been seen wearing Alexander McQueen jackets. He has a fondness for Western-style fashion, including short leather jackets, distressed jeans, cowboy boots, and velvet blazers. He also owns a customized pair of Nike Air Jordan sneakers made from metallic leather with a laser-cut Tesla logo.

This pair was specially created for the billionaire by the California-based company DM Custom Sneakers. The sneakers quickly became a hit, and the craftsmen promptly released a limited edition of the model. Despite the price tag of $1500 per pair, Tesla fans managed to snatch up the sneakers within hours.

Image formation is a powerful tool that helps attract attention, engage customers, and stand out among competitors.