Behold PureWow Editors’ Most Regrettable Y2K-Era Outfits

It was the turn of the millennium…and let’s just say the fashion was fierce. Or was it? We asked our editors to go back through their photo archives (er, bust out those hard copy photo albums) to critique their most regrettable Y2K outfit choices…and let’s just say there was a lot of polyester.

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jillian quint y2k outfit
Jillian Quint/Getty Images

Jillian Quint, Editor-in-chief

“The year was 2000. The future was upon us and I was on my way to get a liberal arts degree in my polyester stretch sleeveless mock turtleneck which was, in retrospect, a nod to both Hermès and the bargain bin at Annie Sez. My hair was pumpkin spice meets Jennifer Aniston and you can’t tell, but I’m wearing a calf-length A-line skirt and square-toed strappy sandals…which are probably back in style, come to think of it.”

rachel bowie y2k fashion
Rachel Bowie/Getty Images

Rachel Bowie, Director Of Special Projects

“The wrap top was from Ann Taylor. (I spent the summer working there as a wardrobing consultant—my official title—and putting every paycheck right back in the register.) The hot pink pencil skirt was Express. But the pièce de resistance was the bubble chain statement necklace that I knew would sparkle in the lights on stage for my end-of-semester a cappella concert. I had a solo to “Walking on Broken Glass” by Annie Lenox that year, so I was dressed to impress and, TBH, I actually don’t regret this outfit. When I see this pic, I remember the magic of that night and how stylish I felt. I do regret the makeup just a tad. I was a bit heavy handed with the blush.”

jenny jin y2k fashion
Jenny Jin/Getty Images

Jenny Jin, Beauty Director

“My friend and I drove to Philly for the weekend to audition for American Idol. We didn't make it to the next round, but we made something that I would argue is infinitely more valuable: memories. I thought this outfit would showcase my cutting edge sense of style to the judges. In fairness, I might still wear that jacket today. I just wouldn't layer two tank tops underneath. And I'd definitely ditch the hair bump. That was my ‘going out’ look that year. You know, saved for those special occasions when I really wanted to look fab. Give it another few years though and I bet some version of the style will come back on TikTok 2.0.”

alexia dellner y2k fashion
Alexia Dellner/Getty Images

Alexia Dellner, Senior Editor

“The jeans were low-rise and the tops were cropped. Even though I specifically went out looking for jeans that were impossibly low, I then paired them with a belt which...makes no sense. I'm also wearing a white bra here under my black tank top. It's not the most embarrassing early 00’s look I ever wore (those pictures have been burned long ago), but it's definitely a style that I would not attempt again (like, ever). And yes, I know low-rise jeans are back and can we just not?”

stephanie sengwe y2k fashion
Stephanie Sengwe/Getty Images

Stephanie Sengwe, Associate Editor

“My hair was permed, flowy bangs were all the rage and front-facing cameras weren't thought of yet, so we took to the bathroom mirrors with our digital cameras. Please note the Aeropostale t-shirt, hand on my hip and perfectly executed duck lips. So much of this is wrong (like, so wrong) but it was also so on brand for the times and so, as embarrassing as it is, I absolutely stand by it.”

cristina gutierrez y2k fashion
Cristina Gutierrez/Getty Images

Cristina Gutierrez, Senior Editor, Branded Content

“It’s the blah grey houndstooth for me. No, wait, it’s the huge pleather belt. No, wait! It’s the Twizzlers. I mean honestly, I can’t defend a single piece of this college look. (Why wasn’t I wearing a cute mini or even bubble top? I could have at least rocked some platform heels.) While my pony does get an A++, the neck down gets a D-. Not totally an F, because hey, at least I attempted to cinch my waist.”

candace davison y2k fashion
Candace Davison/Getty Images

Candace Davison, Executive Editor

“It took three ventures into the depths of Facebook—and a failed attempt to find my old MySpace profile—to unearth this gem. How do I know it's from the early 2000s? You mean, aside from the massive computer tower and lizard CD rack behind me? I've got an extra-long layered cami over a three-quarter length Hollister tee, with flare jeans that are ballooning out of suede wedge boots that have NO PURPOSE EXISTING IN Florida. Even on those three days a year it’s under 55 degrees outside. I'm pretty sure I saw Cameron Diaz wearing similar boots and *had* to have them for Christmas.”

dara katz y2k fashion
Dara Katz/Getty Images

Dara Katz, Executive Editor

“It would be easy to sum up my bat mitzvah look—hair twists, braces, clown makeup and all—as the epitome of cringe, but instead, I’m gonna defend it! I’ve made fun of it for too long, and now I owe it to my 13-year-old self who went all out. That girl didn’t hold back, brilliantly pairing a green sparkly tank from Caché (no doubt designed for a much older demographic) with a take on Lizzie McGuire butterfly clips. Looking back, it emanates high-low 2000s fashion, commenting on the power of Disney, orthodontia and why 13-year-olds should never step foot in Caché.” — Dara Katz, Executive Editor

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Rachel Bowie

Royal family expert, a cappella alum, mom

Rachel Bowie is Senior Director of Special Projects & Royals at PureWow, where she covers parenting, fashion, wellness and money in addition to overseeing initiatives within...
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