This past weekend, the New York Times crowned Jack Dorsey the “Gwyneth Paltrow of Silicon Valley.” Products that the Twitter CEO endorses—personal saunas, sleep tracking devices, and meditation centers—often sell out quickly and generate absurd waiting lists, as men seek to emulate his monastic, new age lifestyle. If Elon Musk’s brand is spoiled rich boy with the best toys on earth, like the super rare Nike Lunar Flyknit HTM NRG, Dorsey’s is suffering monk—in a beautiful $300 T-shirt. “He is very thin,” the Times wrote. “He looks paler than usual. His beard is longer. The lines on his face have deepened, and he can seem to disappear in one of those high-end, overly long T-shirts.”
Curiously, the paper failed to specify that those “high-end” shirts are most often by the goth dude hero Rick Owens. In fact, Dorsey is often fully kitted in Owens’ designs. He wears the long shorts and the tank tops; he wears the bulbous, post-apocalyptic sneakers, he wears the designer’s coveted leather jackets.
This is disorienting for fashion fans who worship Owens. When Chris Anderson, the head of the public speaking conference series TED, posted on Twitter that he’d be interviewing Dorsey back in April and wanted to solicit questions from his followers, one user wrote, “What’s with all the Rick Owens, seriously.” Just a few days before, when Dorsey revealed a tortured wellness regimen that includes intermittent fasting, a Twitter user joked that “Jack Dorsey’s diet seems really bad from a health perspective, but it seems good from a ‘looking good in Rick Owens’ perspective and so I'm fine with it.” Much as Gucci fanatics winced when Kellyanne Conway wore one of Alessandro Michele’s zany red, white, and blue coats to the inauguration in 2016, there’s a dissonance in seeing Dorsey, who continually fails to confront his platform’s growing fascist sector and its role in conveying Trump to the White House, in one of fashion’s most treasured designers.
Dorsey didn’t always dress this way. It began when he grew his beard and became the CEO of Twitter for a second time, in 2015, though not in that order. Back in September 2016, before Twitter’s role in Trump’s ascent was so obvious, Quartz wrote that Dorsey was, compared to dweeby Mark Zuckerberg, “pioneering a different version of the laid-back CEO uniform—one that’s a lot edgier, and much more luxurious.”
To be sure, Owens’s clothing represents a sense of the sumptuous and apocalyptic—as John Jeremiah Sullivan wrote in his GQ profile of the designer last September, it is “part dissolving luxury, part elegant sleeping bag.” You get the sense, with everything Owens makes, that something cataclysmic has just happened, and this uniform is the way forward. His designs, and the universe that is practically requisite with them, don’t inspire fans so much as devotees, or converts, as Sullivan put it: people who sign themselves over to the Rick Owens world, in the same way that people are now emulating, to less joyful effect, Dorsey himself. In fashion, that kind of transformation is gratifying, part of the magic of truly innovative clothing. But that same dynamic, playing out in Silicon Valley as it so often does, inspires the kind of messiah-complex leadership that Dorsey embodies. Underlying Owens’s designs, always, is an optimistic sensibility. But Dorsey is undergoing a highly public performance of suffering, like a living representation of that call center robo-voice saying over and over, “YOUR CALL IS VERY IMPORTANT TO US.”
You wonder what the two would really make of each other if they met. As Owens told Sullivan of what he thinks of while designing, “I'm thinking of my life. I'm thinking of the way I live. I'm thinking I want Brancusi to wear one of my dresses while he's making a piece of art. I'm thinking of Brancusi. I'm thinking of Eisenstein drawings. I'm thinking, ‘I like the way that looks.’”