The clothes put Dorsey more in line with the new generation of menswear consumers, or even one of Owens’s celebrity fans, than a traditional CEO. They also make Dorsey stand apart at industry events. Dorsey and Twitter declined to comment.

Dorsey isn’t alone in courting a more rebellious, yet expensive, style. Vivi Nevo, a financier who has invested in both Twitter and Square, has turned up at the annual Sun Valley Conference dressed similarly. When he and Dorsey are together, they cut a very different figure than the typical attendee.

Jack Dorsey (L), interim CEO of Twitter and CEO of Square, talks with YouTube CEO Susan Wojcicki (C), as venture capitalist Vivi Nevo (R) walks with them during the first day of the annual Allen and Co. media conference in Sun Valley, Idaho July 8, 2015. REUTERS/Mike Blake - RTX1JMLJ
Here they are with YouTube CEO Susan Wojcicki.
Image: Reuters/Mike Blake
Aviv 'Vivi' Nivo, Jack Dorsey, and former McDonald's CEO Steve Easterbrook at Sun Valley
And here they are with McDonalds CEO Steve Easterbrook.
Image: Drew Angerer/Getty Images

It may not be too surprising to see Dorsey, 39 years old, wearing high-end fashion. Men in general have become more interested in clothing and their appearance over the past several years. That doesn’t mean we should expect to see the next generation of male Silicon Valley CEOs ditching their hoodies and button-ups, but maybe a few will opt for a leather jacket instead.

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