Amazon founder Jeff Bezos made headlines this week when he announced that he would step down as CEO of the company he founded in 1994 to focus on philanthropy and his media and space-travel businesses.
While Amazon the company has had mixed success with its foray into high fashion, in recent years Bezos has become an unwitting fashion icon, turning up at fashion shows seated next to Vogue’s Anna Wintour and showing off his trim figure in tailored suits and casual/chic outfits that have none of the nerdy vibe often associated with tech executives.
Things, however, weren’t always that way for Bezos, who looked quite different when he founded Amazon from his garage in Seattle and went on to become the world’s richest man.
Bezos had a makeover of sorts in the early aughts, when he started to focus on his physical appearance and personal style, as these pictures show.
In December 1999, Bezos appeared on The Tonight Show with Jay Leno for an interview in which he showed a toy available on his superstore. His receding hairline and attempt at a suit – a mismatched baggy jacket-shirt-and-trouser combo – are a far cry from the stylish fits of the Bezos of today.
Bezos kept a very low profile in the first decade of the 21st century, making few appearances and focusing on his fast-growing business. On a visit to New York in 2002, after Amazon posted its first quarterly profit, he looked upbeat, but his ill-fitting jacket paired with equally ill-fitting khaki pants said otherwise.
Fast-forward a decade and Bezos looks like the epitome of the successful Silicon Valley mogul (yes, we know that Amazon was founded in Seattle but you get the idea) at the Allen & Co. Media and Technology Conference in Sun Valley, Idaho, in 2013. Accompanied by his then wife MacKenzie, he sported a T-shirt that showed off his bulging biceps, styled with a zipped vest, denim pants, Converse sneakers and his signature Ray-Ban sunglasses. He could have done without the baseball cap but the look is still very on point – and on brand.
In 2015, Bezos looked ready to star in the remake of Top Gun at the maiden voyage of a rocket from Blue Origin, his aerospace company that he hopes will be a key player in the nascent space-tourism industry. He paired his signature Ray-Ban sunglasses with a soft shell jacket emblazoned with the company’s logo.
With the founding of Amazon Studios, Bezos also became an entertainment mogul, which means lots of chances to mingle with the glitterati set in Hollywood. In this picture, taken at the Amazon Studios’ Golden Globes Celebration in Los Angeles in 2018, Bezos looks like the life of the party clad in a tuxedo and surrounded by Hollywood stars Matt Damon, Taika Waititi and Chris Hemsworth.
Bezos is a fan of Italian designer Brunello Cucinelli’s relaxed – and very expensive – tailoring. This check-pattern jacket, cleverly paired with a chambray shirt and suede belt, is a clear influence of Cucinelli’s casual but luxurious aesthetic on Bezos, who has even visited Cucinelli’s headquarters in Umbria, Italy.
Bezos officially became a fashion influencer when French swimwear brand Vilebrequin relaunched a pair of its US$260 swimming trunks produced as part of its 2014 spring/summer collection after Bezos was seen sporting the trunks in 2019 while on vacation with his girlfriend Lauren Sanchez. His fans noticed the octopus-print trunks he wore while on holiday, and thousands searched for them online.
Bezos made a true fashion statement at his first public appearance with Sanchez at an event in Mumbai, India, in 2020. He wore a wildly patterned evening jacket that was departure from the all-black tuxedos he previously wore at glamorous events such as the Met Gala or the Oscars.
Not long after, in February 2020, Bezos jetted off to Los Angeles to attend a Tom Ford fashion show. He matched Sanchez in an all-black tailored outfit and sat next to fashion’s reigning queen Anna Wintour, cementing his role as a stylesetter and fashion icon in the making.
