Photos: We heard Y2K fashion is coming back. So we sent a camera to the Haight to see it IRL

Walking around Haight-Ashbury these days can feel like a time warp. No surprise there. For some living in this neighborhood, the Summer of Love never really ended.

But we aren’t here to talk about Acid Tests or girls with flowers in their hair.

On today’s Haight Street, wide-legged JNCO jeans are making a comeback. Crop tops and low-rise denim, with accompanying midriffs, are in. Chunky shoes and shield sunglasses are in abundance. And most of these sartorial statements will be found on a younger set of tweens to 25-year-olds.

None of this is news, per se. It all began around 2021 and has been written about extensively by self-conscious journalists of a certain age. Yes, Y2K is all the rage, at least for Gen Z, a cohort that is reportedly descending upon our fair city in droves.

For those who lived out their teenage years in the late ’90s to early 2000s—as yours truly, a dyed-in-the-wool millennial, did—it can all feel like an awkward throwback to the turn of the 21st century, and those even awkward-er middle and high school days.

But as members of The Fourth Estate, it is our solemn responsibility to look squarely at the uncomfortable truths of the world. And so, we sent a photographer to document all the ways in which the kids are putting a fresh spin on all the old duds we finally cleared out of our mom’s basement during the pandemic.

At Wasteland, one of the many vintage and thrift clothing boutiques on Haight Street, they’re having trouble keeping anything bright, colorful, small and cropped on the shelves, according to Charlie Giling. The 19-year-old retail associate, who was working the cash register on a recent Friday, said fashions that evoke the era of That’s So Raven and Hannah Montana on Disney Channel are so fetch. 

“There's an edge to it that's like washed-up pop star almost. And people… they’re drawn towards that,” said Giling, as well as the nostalgia factor of shows they grew up with. Mini skirts, chunky sneakers and face-covering frames are also popular items, he says. 

Meanwhile across the street at vintage thrift store Held Over, sales associate and visual merchandiser Madrid Quesada is noticing people sporting fashions that are already bleeding into the later 2000s and early 2010s, with looks inspired by TV shows like The Vampire Diaries and Gossip Girl. Bedazzled BB Simon belts and little tank tops are also sought-after items, and customers are also seeking ’70s-style clothes—probably because of the popularity of That ’70s Show at the turn of the millennium, the-24-year-old theorizes.“When we do get stuff that is like early 2000s, it sells immediately,” said Quesada.

While Giling thinks that Gen Z is embracing Y2K fashion to relive their not-so-long-lost childhoods, Quesada also chalks it up to the natural fashion cycle as well as TikTok. As some have observed, the internet, social media and streaming services seem to be accelerating the pendulum’s swing. But Quesada also thinks that Gen Z is making an ironic wink to previous generations by reappropriating their decade-defining styles.

“Knock-off is funny. And some people wear it out of humor, but it's also like high fashion to them,” said Quesada, a native San Franciscan from the Excelsior, who also studied fashion merchandizing at City College.  Roman D'Argenzio, the proprietor of vintage tee shop Trove SF has been noticing more shoppers gravitating toward band shirts from the early 2000s. He also attributes the return of Y2K fashion to the perpetual ebb and flow of thrift store inventory, but goes one step further.

“Vintage secondhand clothing almost determines what the big, fast fashion companies are going to make,” D’Argenzio said. “Because the kids at the thrift stores, the creative ones, are the ones that are like putting outfits together and making it new.” 

Another trend Giling is noticing—an inclination to buck trends altogether. 

“I just think what people are doing now is they're moving beyond trends and just focusing on individuality,” he said. “That's what's selling more: People are putting all these crazy pieces together and making outfits that they find.”  So maybe the “Y” in Y2K now stands for “you do you”? Either way, the kids are certainly no longer into skinny jeans.

Photos by Eloïse Kelsey