When visiting my hometown in Northern California last summer—a little city nestled in a valley of redwood trees, populated by a happy mix of old hippies and young yuppies, dive bars and wine bars—I went downtown to get some ice cream with my kid. As we approached the shop, three teenagers walking by stopped me in my tracks.
I couldn’t take my eyes off them as they passed us, heading down to the park where I used to loiter and smoke cigs as a restless teen. Their baggy jeans—so long and wide you could barely see the rubber toes of their colorful Converse—were slung below their hips, leaving just enough room for their white boxers to peek out above the waistband. They wore cropped baby tees; sparkly belly button rings glistened in the afternoon sun. Their long hair was held back with big claw clips, and one of them had several plastic butterfly clips—purple, pink, and blue—adorning her blond waves.
Was this some sort of joke? Why were they dressing like they were my friends and me heading to 7-Eleven to get a peach Snapple in 1998? Why would such a moment in sartorial history ever dare to repeat itself? Was I in a time warp? Is this how my parents felt when bell-bottoms came back in style? Are they trying to make me feel old? How old am I? So many questions…
Instead of rambling on about the subtle horror of watching the trends your generation started come back in style, I decided to consult a professional. Darcy Barber has worked in the fashion industry for decades, and in trend-forecasting in particular, for major brands like Champion and Aerie, since 2012. She is currently helping several startups in the strategy stages of launching apparel lines, and generously offered to help me figure out what on earth is happening with these youths.
Q: Is this the first time the late ‘90s/Y2K trends have resurfaced?
A: Yes and no. I would say, it’s the first time as a unified aesthetic. For example, cargo elements and utility details never really disappeared from the zeitgeist, but those paired with crystal-embellished, candy-colored sunglasses with micro-scarf tops, trucker hats, and baguette bags all worn together? I would say yes, this is the first time we’ve seen them reunited—and the jury’s still out on whether it “feels so good.”
Q: Why now?
A: Collective conscience! With the rise of AI, it’s perfectly obvious times are a-changin’—and at a clip that will be hard to outrun this time around. I remember back to the Y2K bug when I had a high school friend whose parents thought the world was going to end, or at least that society would launch into systematic chaos at midnight on December 31, 1999. In response, they flipped on the prepper switch and stored gallons and gallons of water, etc. There was a palpable fear around what the internet could do to us, and now, 23 years later, what the internet could become. We’re right back there at a tech evolution crossroads. This time around, the machines might just take over!
With that comes a healthy dose of anxiety. As it’s been reported ad nauseam, Gen Z-ers as a whole have unprecedented levels of stress, anxiety, and loneliness compared with previous generations. As the pendulum swings, it’s not surprising that we see Y2K trends coming back today. By definition, they were extremely playful, steeped in a bubbly World Wide Web naivety; a nostalgia for simpler tech times, when the Internet was just a ‘lil baby: simple, less scary, more fun!
Q: Is it the same for the ‘90s styles that are back?
A: This might be an unpopular opinion, but I have a theory: Slip dresses and flannels, overalls and grunge, etc. are just a millennial version of Y2K for Gen Z. Same easy breezy casual feelings, but more palatable for an “older” woman.
Q: How long does it take for a trend to resurface? Is this the usual timing? Like about 20 years?
A: Twenty years is the industry norm, but design and merchandising technologies have greatly reduced the speed-to-market, and social media makes it so trends rise and fall literally overnight (watch the Shein doc on Hulu, ugh!). Companies spend a boatload of dough tracking the cycles. The flow goes like this: introduction, rise, peak, decline, obsolescence.
Q: What makes a trend come back?
A: I have this grassroots odd theory that whatever is in thrift stores at scale becomes popular again, trickles up from youth to runway, and then back down to the masses, and so the cycle continues. How else would kitten heel pointed-toe mules ever have made it back into the conversation!?
Q: Who starts the trends?
A: In America, we live in a youth-obsessed country, and the young innovate in a way that’s unconcerned with conventional paths. But we cannot talk about trends without stating that Black culture is one of America’s biggest exports—and let’s be honest, probably the biggest. I truly think that marginalized communities, kids that aren’t rolling in green, and artists and visionaries who lack traditional resources reinterpret fashion with the tools they have—and it’s magic! Just look at Telfar Clemens. Genius!
Q: What are some of our old trends that are super popular among Gen Z now?
A: Platforms, chunky shoes, crop tops, tube tops, wife “pleasers,” crochet, chunky belts, low-rise denim, velour sweatsuits, body chains, handkerchief hems, butterflies, candy-raver vibes, exposed underwear, rhinestone tees, cargo pants, micro-minis, baguette bags, wrap sunnies, mini specs, oversized, chaos… just to name a few.
Q: Do you have any tips for wearing a trend your generation first created?
A: I definitely have feels about this. On one hand, no, I’m not gonna wear what I wore in my ‘best dressed’ yearbook pic from 2000: a cropped bubblegum pink fuzzy hoodie with a micro-mini patent leather backpack, complete with a fur poof keychain paired with denim pedal-pushers and chunky wooden strappy platforms. I’m way cooler than that now (lol)! On the other hand, I’d prob wear the exact same hoodie, but in a color that feels more me, like a muddy chartreuse. I’d gladly wear the same mini backpack, perhaps without the Barbie graphics and in real leather—maybe a snakeskin? You see where I’m going with this? I’ll just end by saying, lean into curiosity, not fear. Fashion is fun and expressive. Only adopt trends if they’re you. Your unique personal style is light-years more authentic.
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Megan Cahn started her editorial career at Sassy’s less irreverent younger cousin, CosmoGIRL. She went on to work in the women’s lifestyle space at publications such as ELLE, Refinery29, Cup of Jo, and Best Life. She lives in Brooklyn with her husband, cat, and five-year-old daughter, who has adopted her childhood Cabbage Patch Kids collection.
