Twitter’s Jack Dorsey represents the next step in the evolution of Silicon Valley style

Cool jacket.
Cool jacket.
Image: Reuters/Lucas Jackson
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If there’s one industry in the US changing corporate dress codes, especially among men, it’s technology. Apple’s late founder, Steve Jobs, in his uniform of jeans and a black turtleneck, helped reimagine what a CEO should look like. Today, the exemplar of Silicon-Valley casual has become Facebook founder Mark Zuckerberg, who is so synonymous with gray t-shirts that someone created a website last April Fool’s day advertising a fake Zuckerberg line for H&M.

But Jack Dorsey, who heads both Twitter and Square, is pioneering a different version of the laid-back CEO uniform—one that’s a lot edgier, and much more luxurious.

Dorsey often turns up at industry events in a leather jacket over a t-shirt, wearing jeans and sneakers. What separates them from the typical style of Silicon Valley CEOs is that these clothes are often by Rick Owens, including the “Island Dunk” sneakers Dorsey wore while rallying his staff earlier this year, or the jacket he donned for his media appearances at the time of Square’s IPO in November 2015.

Owens’s clothes are experimental, aggressive, and very high-end. His t-shirts, which look pulled like taffy, run between $200 and $300 each. His leather jackets, which originally made his name, routinely cost upward of $2,000.

Square CEO Jack Dorsey is interviewed on the floor of the New York Stock Exchange, Thursday, Nov. 19, 2015. (AP Photo/Richard Drew)
Image: AP Photo/Richard Drew
SUN VALLEY, ID - JULY 6: Jack Dorsey, co-founder and chief executive officer of Twitter, attends the annual Allen & Company Sun Valley Conference, July 6, 2016 in Sun Valley, Idaho. Every July, some of the world's most wealthy and powerful businesspeople from the media, finance, technology and political spheres converge at the Sun Valley Resort for the exclusive weeklong conference. (Photo by Drew Angerer/Getty Images)
Image: Drew Angerer/Getty Images
Jack Dorsey and Kate Greer seen at the "Psychos" by Babe Walker Book Party at Alice and Olivia on Thursday, May 2, 2014, in New York, New York. (Photo by Hal Horowitz/Invision for Little Body LLC/AP Images)
Image: Hal Horowitz/Invision for Little Body LLC/AP Images)

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.