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Jeff Bezos’s transformation hasn’t gone unnoticed. But what has been making news recently is his dressing style when he steps out with girlfriend Lauren Sanchez. The most popular has been a pair of swimming trunks from Vilebrequin’s 2014 Spring-Summer collection that the Amazon founder wore while holidaying in the Mediterranean. With his stamp of approval, the octopus print trunks (retailing at $260) became the hottest menswear item of the summer, with shoppers searching for them more than 4,000 times between July and August, according to a fashion search site.

Say what you must about his diet, but the evolution of Jack Dorsey’s footwear style is fascinating. From loafers to statement sneakers to thong sandals, the Twitter CEO knows a thing or two about shoes. In 2017, the Internet went into a frenzy when Dorsey was spotted wearing thong-style sandals for a talk with former Goldman Sachs CEO Lloyd Blankfein. Since then, the sandals have become a part of Dorsey’s wardrobe.

Most recently, he sported the Earth Runner sandals at the Square Crypto inaugural off-site. Starting at $69, the sandals are said to combine the barefoot benefits of earthing shoes (shoes that offer the primal experience of living grounded to the earth) with the functionality of minimalist running sandals.

Apple co-founder Steve Jobs had the black turtleneck and Mark Zuckerberg has a closet of grey T-Shirts. But Zuckerberg doesn’t just wear any old plain grey T-Shirt. His are specially ordered from Brunello Cucinelli, and reportedly cost between $300 and $400 each. The Facebook CEO has said earlier that clothing, along with breakfast, is a “silly” decision he doesn’t want to spend too long making.

Earlier this year, when Tesla launched the new Model Y car, it wasn’t the car that caught everyone’s attention but CEO Elon Musk’s flashy custom-made sneakers that sported the Tesla logo emblazoned above the toe box.

According to shoemaker DM Custom Sneakers, the Nike Jordan 1 sneakers were reconstructed as a gift for the billionaire using quality materials such as premium python and hair on hide leather. Following the global attention that Musk’s sneakers received, DM Customs decided to make six more pairs of the ‘Tesla shoe’ at a price of $1,500 apiece.

Unlike the rest of Silicon Valley, Instagram co-founder Kevin Systrom’s wardrobe eschews the typical hoodie. The tech entrepreneur is more comfortable in sports coats and ties. “I’m probably the only guy in Silicon Valley who enjoys wearing a jacket or a tie and does it unironically,” he has said earlier.

“My jacket of choice is a Boglioli unstructured jacket. It almost looks like a sweater. I can wear it to anything in Silicon Valley and I don’t look like a stiff or a banker.”

For a formal event, Systrom loves wearing Brioni suits for “that old Italian style”.

(Image: Instagram/Kevin Systrom)

If there’s one item that Silicon Valley CEOs can agree on, it’s Lanvin sneakers. The Parisian high-fashion house makes chunky, low-top sneakers that are favoured by tech bosses like Satya Nadella (L), Sundar Pichai (R) and Larry Page (C). Systrom also once said he prefers the high-fashion Parisian brand because they are easy to pair.