A few months ago, a longtime friend from California came to New York for a conference, and called to see if I was around for lunch. He lives in San Francisco and works at a publicly traded social-networking site in Silicon Valley, and we planned to meet at the Columbus Circle monument. I arrived early, got coffee, waited. And waited. But no one was there: just a picnicking couple and an old dude in relaxed-fit chinos and a Gore-Tex shell. I got up to leave. Then the old dude yelled my name.

I hadn’t recognized my friend—all of 28 years old! He’d registered far beyond the limits of my sexual radar. The reason why, up close, was obvious. He was wearing Rockports. He’d been living in San Francisco too long.

I grew up in that city, and still love it. San Francisco does many things better than most: bridges, hills, car chases, skateboarding, sourdough, fog, and earthquake preparedness—but never, ever men’s fashion. S.F. style is the clothing equivalent of water: The taste is so neutral, you can’t be sure it’s there. Money might be transforming the city in other ways, but its clothing will remain forever comfy and functional.

“New York, to me, always had a sense of trying too hard,” says Jarrett Fuller, 24, who moved to San Francisco from Dumbo last spring to work at another publicly traded social network. Since going west, Jarrett has been wearing the exact same outfit every day for a year: a white cotton collared shirt tucked into jeans with a brown belt. (He owns multiples of each.) The guy who sits next to him at work is considering a similar regime.

This mentality is all about letting your ideas do the talking, says Woods Buckley, a Bay Area native and Google employee who describes a local uniform of free company T-shirts. “There’s an appreciation of not spending money on clothing.” Transplants from afar, like London or New York. will often arrive at Google in “a jacket, nice slacks, formal shoes,” Buckley says, only to undergo a swift transformation into short-sleeves and Patagonias, or “Patagucci,” as he and his friends call the pricy fleeces. Buckley reports that he has never seen a single cuff link at Google. He did, however, recently order a pair of Betabrand “Dress Pant Sweatpants,”a kind of trompe l’oeil pant tailored for the boardroom but constructed out of terrycloth.

If the comfort imperative seems at odds with the industrious young people who embrace it, consider that elastic waistbands are equally useful for an active lifestyle. “You need to be able to hike, bike, or surf at a moment’s notice,” says Alex Crane, who grew up in the city and now works as a designer at Jack Spade. This means Giro wind-resistant cycling shells and antimicrobial stink-resistant pants from Levi’s Commuter Collection. As a stylish male, Crane grew up with conflicting feelings about his sartorial landscape. “San Francisco is a breeding ground of progressive ideas, from Kerouac and the beatniks to Haight Ashbury to the gay rights movement, and style was intrinsic to all of these social revolutions,” he says. “On a basic level, I love the idea of dismantling traditional masculine formality. The problem is that the current outcome is a style I just don’t like.” Specifically, Crane says, he wishes San Franciscans weren’t so averse to sacrificing a smidgen of comfort for style. “Aesthetics have a value,” he says. “It’s not a trivial thing.”

If culture is partly a result of who is attracted to a given locale, it makes sense that those enticed by San Francisco’s temperate climate would likewise gravitate toward soft, moisture-wicking zip-ups. And when standing atop one of the city’s many skyscraping hills—letting your gaze fall upon the cake-decorated Victorians, the eucalyptus groves, the glittering bays—it’s equally easy to imagine the city’s residents, encountering beauty wherever they look, finding themselves utterly uncompelled to compete. This approach to fashion used to be seen as endearing—just one of many qualities that kept San Francisco feeling like an exception to nearly every urban rule. But at some point over the past ten years, it took on a note of derision. Right around the time Facebook moved to Palo Alto, Vice started brutalizing San Franciscans’ clothing choices in their Do’s and Don’ts column. In 2010, The New York Times’ Guy Trebay dubbed the Bay Area “the land that style forgot“, and a year later, GQ named San Francisco one of the worst-dressed cities in the nation.

But plenty of of people in plenty of cities have no style. What irritates observers is not the aesthetic but, rather, its latest adopters. These more recent San Franciscans—the Dropbox data scientists, the Square engineers—are presumed to be rich, which implies that their indifference to Riccardo Tisci comes from a principled renunciation rather than a lack of choice. We get touchy whenever we see members of an enviable tier doing something the rest of us can’t, whether it’s flying private or wearing the same outfit for 12 months without an intervention. For outsiders, formal sweatpants can mean only one thing: In San Francisco, you don’t have to dress for the job you want, because if you can afford to live there, you probably already have it.