It’s 1996, and Bill Gates, dressed in his signature look—wire-frame glasses and a crewneck sweater over an open-collared shirt—sits across the desk from a suit-and-tie-wearing Jay Leno on The Tonight Show. Leno’s pointed jokes about casual dress code prompt groans of sympathy for the rumpled billionaire. 

“In the computer world, they were saying you sort of set a fashion trend,” Leno says. 

“The trend must be not to pay much attention,” Gates replies. Then he continues: “When you really want to hire people who are the best, you can’t be too picky about what they wear.” 

Safe in its 1990s dot-com bubble, Microsoft blissfully ignored the norms of corporate style. But corporate style couldn’t ignore Microsoft: Thanks in part to the Redmond-based company’s laissez-faire attitude, workplace culture in the tech industry and beyond would never look the same. 

Programmers began asking why they should put on “a coat and tie when they could work for Microsoft in shorts and sandals,” and the philosophy grew wings, per a 1996 Seattle Times article. Consciously unchic, occasionally Seattle-influenced fashion, like sensible outerwear and ill-fitting polos à la the infamous Windows 95 launch, became tech industry staples. As CEO Satya Nadella said in 2018, people work at Microsoft “not to be cool, but to make others cool.”

Does that devil-may-care aesthetic of yore still align with an industry whose titans now quite literally run the country? Microsoft execs haven’t traded their function-over-form ethos for gold chains and a seat at the inauguration platform like some other moguls. But even Seattle’s tech workforce has started to look in the mirror.

There’s this pervasive idea that if “you work in tech, you kind of dress like a slob,” says Adrian Eames, founder of local menswear boutique Eames NW. Some have chosen to “go the complete other direction and say, ‘I know there’s a stereotype that software engineers don’t care, but I actually do,’” Eames says. After all, these companies aren’t ragtag startups anymore.

But that’s not the only way that fashion has adapted to changes in the industry. As tech leaders become the designer-suited main characters of a corporate America they once flouted, streetwear finds inspiration in the platonic ideal of the twentieth-century programmer instead. Fashionable young men don wire-frame specs, bulky shoes, and plaid dress shirts. Etsy sellers hawk vintage Microsoft merch featuring serif fonts and pixelated icons. The more retro, the better: Think high-fives in the cafeteria, not handshakes in the boardroom. 

It’s a nostalgic style that yearns for an era when tech companies felt scrappy, creative, and promising—like the nerdy underdog who managed to make it big. 

And it looks a lot like Bill Gates did sitting across from Leno.