All the Cringy 2000s Outfits We're Trying to Re-Create Today

Fashion in the early 2000s was weird. There, I said it. From what I personally remember as a try-hard 7-year-old, I was obsessed with capris and tube tops, tiny knock-off Louis Vuitton shoulder bags (sorry, but my mom wouldn't buy me a real one), and any sort of flip flop style imaginable. With that said, the women featured ahead were my icons at one point in time (Britney Spears still is but that's a conversation for another day), so when I say these outfits make me cringe, it's not because of them—it's because of me.

At some point during the early 2000s, I tried to dress exactly like all of my celebrity icons—Lauren Conrad, Mischa Barton, and so on and so forth. What they wore was it back then and recently, while I was craving a bit of nostalgia, I realized that it's not just the '90s that have made a major comeback, it's the 2000s as well.

From tie-dye to low-rise jeans, the eight celebrity outfits from the decade everyone loves to hate are bound to have you cringing and smiling and shopping all at once. And the craziest part is, once you see the outfits ahead re-created, you'll realize you have probably one more or more of them in the past six months or so. You'll see.

celebrity-outfits-2000s-286872-1587512333096-image

(Image credit: Getty Images)

Pictured: Rihanna, 2005

Low-rise jeans are back, whether you like it or not, and this summer the coolest way to wear them is with anything and everything tie-dye. Take it from old-school Rihanna and grab yourself a tie-dye tank and some classic Chucks and you've got yourself a Rihanna-approved 2000s-inspired look. 

Get the look:

celebrity-outfits-2000s-286872-1587512332276-image

(Image credit: Getty Images)

Pictured: Jessica Simpson, 2000

A leopard-print coordinating set? Yeah, she did that. While the exact look above might induce a tiny bit cringy, back then, this look was it. When you see the Miaou set below, you'll be reminded that this is, in fact, still very much a vibe. 

Get the look:

celebrity-outfits-2000s-286872-1587512327499-image

(Image credit: Getty Images)

Pictured: Britney Spears, 2000

To be honest, if I could find pants close enough to Britney's I would have shopped our the exact ones, but since I had no such luck, I did the best next thing: a Paco Rabanne bag. These very Zenon: Girl of the 21st Century–esque large sequins will trigger that sense of early-2000s nostalgia, no matter where you place them.

Get the look:

celebrity-outfits-2000s-286872-1587517317176-image

(Image credit: Getty Images)

Pictured: Ashley and Mary-Kate Olsen, 2001

Be honest—when was the last time you put on a halter top? If it was almost 15 years ago, you're not alone, but what we've learned over the past couple of months is that the slinky top is making a major comeback. So when you finally muster up the courage to put one back on, be sure you channel the Olsen's energy.

Get the look:

celebrity-outfits-2000s-286872-1587512330326-image

(Image credit: Getty Images)

Pictured: Destiny's Child, 2000

Never has an outfit from the early 2000s felt more like me. Tiny tie-dye tops, leather pants, and pastel shoes? Color me thrilled that all of these things are more than relevant again.

Get the look:

celebrity-outfits-2000s-286872-1587512334473-image

(Image credit: Getty Images)

Pictured: Sarah Jessica Parker and Kim Cattrall, 2000

Tube tops as evening wear? Sarah Jessica Parker did it best. The polished aura of the monochromatic color scheme combined with the dripping crystal rhinestone necklace gives me all the feels and will 100% breathe new life into your formalwear attire. 

Get the look:

celebrity-outfits-2000s-286872-1587512331422-image

(Image credit: Getty Images)

Pictured: Hillary Duff, 2001

Sorry, but we only know Hillary Duff as Lizzie McGuire when she looks like this. The frilly dress, Tiffany's silver heart necklace, and strappy sandals were a vibe then and are even more of a vibe now (minus the necklace). 

Get the look:

celebrity-outfits-2000s-286872-1587512328895-image

(Image credit: Getty Images)

Pictured: Cameron Diaz, 2002

One-shoulder tops are the new camis of 2020, but oddly enough, the early 2000s did the trend first. Funny how everything always comes back around. 

Get the look:

Lauren Eggertsen
Editorial Director

"Copy (200 words): Lauren Eggertsen is currently the editorial director of Who What Where and has worked at the company for nearly seven years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Sydney Sweeney, Lindsay Lohan, and Megan Fox. 


She has also attended multiple fashion weeks, including New York, London, and Milan, where her personal style has been featured on sites such as Elle.com, HarpersBazaar.com, and Vogue.co.uk. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.