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

April 24, 2020 at 05:05AM

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.

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. 

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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. 

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.

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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.

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.  

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. 


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). 

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. 

Next up, shop the five random summer trends I’m stocking up on before anyone else. 

Author Lauren Eggertsen | Whowhatwear
Selected by CWC