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The Amazon cofounder's style and persona have changed a lot over the years, from bookish founder (quite literally in Amazon's early days as a bookseller) to space cowboy at Blue Origin and a Vogue photo shoot.
Here's a look at Bezos' fashion transformation over the years:
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In Amazon's early days, Bezos wore pretty run-of-the-mill business attire.
Amazon was originally an online bookseller.Getty Images
Here he is again in a similar outfit, donning a blue dress shirt, black jacket, and beige trousers.
Early photos of the Amazon founder often show him in khaki pants.Getty Images
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He occasionally opted for this pretty standard combo of a sweater over a collared shirt.
Bezos wears a sweater over a collared shirt in the early days of Amazon.Getty Images
Over the years, Bezos started swapping his khakis for blue jeans more frequently.
Bezos often paired blue jeans with a button-up and jacket.Phillip Faraone/Getty Images
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In fact, he frequently wore jeans when speaking at Amazon events.
Bezos projected a more casual look with jeans.Ted S. Warren / AP
Of course, Bezos dressed in more formal business attire in certain cases that necessitated it.
From left to right, Jeff Bezos, Larry Page, and Sheryl Sandberg.The Washington Post/Getty Images
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Bezos made some changes to his style handbook around 2017.
Jeff Bezos, right, and his brother, Mark Bezos, left, in 2017.Amy Harris / Invision / AP
And who could forget one of his most famous looks?
Jeff Bezos sported a polo and vest to Sun Valley in 2017.Drew Angerer/Getty Images
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At Blue Origin, Bezos embraces another look entirely: Western-inspired spaceman.
Jeff Bezos walks near Blue Origin's New Shepard suborbital spaceship after flying into space.Joe Raedle/Getty Images
Donning a cowboy hat and boots with his blue flight suit, he's another Bezos entirely.
Bezos' cowboy hat completed the look.Joe Raedle / Staff / Getty Images
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A Vogue spread on Bezos and fiancée Lauren Sanchez further cemented the image.
In his off time, particularly since he stepped down as CEO of Amazon in 2021, Bezos varies his outfits a lot more.
Jeff Bezos and his fiancée, Lauren Sanchez.MEGA / Getty Images
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While on a ski trip in Aspen, Colorado, Bezos and Sanchez looked cozy.
Jeff Bezos and Lauren Sanchez in Aspen.BG041/Bauer-Griffin
Here's the couple at a fashion show last year.
Lauren Sanchez and Jeff Bezos attend the Staud fashion show in September 2023.Paul Morigi/Getty Images
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Of course, Bezos attends plenty of galas, fundraisers, and other social functions, as you'd expect of one of the world's richest men.
Jeff Bezos and Lauren Sanchez attended the 2024 Met Gala.Kevin Mazur/Getty Images
Bezos and Sanchez looked considerably more casual trying to blend in with the crowd at Coachella.
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He sported one of his most fun looks while ringing in 2022 with Sanchez.
Amazon founder Jeff Bezos parties at New Year's with fiancée Lauren Sanchez.Instagram / Jeff Bezos