Why Your Younger Co-Workers Are Dressing Like It’s the Year 2000

Nostalgic Gen Zers are showing up to work in clothes and accessories that evoke Y2K style.

Today’s young professionals look a lot like we did 20-plus years ago. I can’t tell whether they are saluting or trolling us.

Why Your Younger Co-Workers Are Dressing Like It’s the Year 2000

They’re embracing 2000s style in boxy Abercrombie & Fitch tees and wide-leg pants. Some are even spending $250 or more in vintage shops so they can pull on the literal same pairs as their predecessors. TikTok is awash in videos with phrases like “Y2K office inspo,” featuring tips on how to dress like the long-lost Backstreet Boy or Destiny’s forgotten Child.

Fashion is cyclical, but that doesn’t explain the resurgence of wired headphones and plastic Nalgene water bottles.

Then there’s the trend of introducing something by saying such-and-such or so-and-so “has entered the chat.” It’s a play on the alert that heralded a new participant in online chat rooms of the 1990s and aughts, a time when many of this phrase’s current users weren’t born.

Maybe members of the next generation are simply recognizing how cool we were, and want to crib everything from our clothes to our hydration habits.

Or, their imitation is akin to patting us on the back while planting a “kick me” sign.

Wearing it bolder

It is possible that younger colleagues are paying homage and poking fun at the same time.

For comfort, it’s hard to beat the sort of roomy cargo pants you would’ve found in the closets of Brad Pitt and every frat bro circa 2000.

For a shot of superstar energy, there’s nothing like the kind of crop top Britney Spears helped popularize around the same time. (So I’m told.)

The 20-somethings bringing back these styles aren’t exactly spoofing those of us who sported them when “Oops!…I Did It Again,” was a hit on MTV. We were on to something.

But we didn’t dare wear any of this to work. We readily accepted that covering midriffs and visiting a tailor were office requirements.

Now we sit in meetings next to recent grads in baggy pants and corporate crop tops. They blur the line between personal and professional attire with a confidence that seems to jest at our conformity: Didn’t you sheeple know the rules are made up?

“I don’t know if it’s a joke on us, but I think it’s one of those things where we just have to laugh at ourselves and be like, ‘Did we really have to be so serious?’ ” says Ebony Boyd, 34.

Starting with her first teenage job 20 years ago, Boyd took a traditional approach to dressing for work because, well, that’s what was expected. Now an assistant director of integrative student services in the business school at Wake Forest University, she’s a bit jealous of budding professionals’ boldness.

One grad student recently shared her plan to dye her hair pink for a career fair. The idea was to weed out any prospective employer who wouldn’t welcome her unconventional look.

Boyd suggested it might be wise to land a job first, do it well for a while, and then unveil a flashier style. Still, she can’t help but admire the chutzpah of a candidate who channels the rocker Pink.

The move isn’t so much about hair as it is about turning the table on a company to judge whether it’s the right fit for you. Boyd sees people with little or no experience taking a job-hunting approach she didn’t dare try until she was established in her career.

Simpler time

The Gen Zers thrifting Juicy Couture and FUBU jerseys aren’t necessarily engaging in some kind of social commentary on the people who wore them originally. When I stopped a few young shoppers in a secondhand store, they said they simply liked the styles they’d seen on social media.

But some are copying the Y2K aesthetic in a deliberate nod to the past.

“The present day is kind of spiritually similar to the 2000s,” says 36-year-old Karlton Miko Tyack, who has a desk job with an auction house in New York and covers menswear and gear as a freelance writer. “If you think about what the aughts were culturally, there was reverence and fear about technology and how it would affect our interpersonal relationships. This is all very familiar.”

Those past concerns seem relatable yet quaint. We used to worry about online chat rooms where it was unclear who was really behind the screen name. Now we wonder whether there is even a human on the other end—or a bot that might fuel someone’s dangerous paranoia.

Personal stylist Ekaterina Kravchenko, 37, says young people are gravitating to clothing and accessories from the early 2000s. This is partly because they perceive it as a time before technology went too far and the world started moving too fast.

When you’re tired of keeping up with the latest status water bottle (Stanley? Hydro Flask? Owala?), you reach for an old-school Nalgene. If you’re sick of AirPods tumbling to the floor, running out of battery or connecting to your laptop when you’re trying to make a phone call, you get nostalgic for wires.

Kravchenko says one of the most coveted items among Gen Z women in New York is a vintage Fendi Baguette, a favorite purse of Sarah Jessica Parker’s character in “Sex and the City.”

“Some of them were made of nylon, so they’re not fancy material,” Kravchenko says. “But it’s almost like the last chance to use something that people had before all the technology took over and we became kind of disconnected.”

Young professionals who wear what was trendy when they were in diapers can look like they’re engaging in cosplay. Indeed, Y2K dress-up days are popping up in workplaces and on college campuses.

It’s getting harder to tell the costumes and everyday wardrobes apart. As someone who once stocked his dresser with Aéropostale, I choose to take the revival as a compliment—even if it is laced with irony.

Write to Callum Borchers at callum.borchers@wsj.com