15 Unforgettable (& Totally Regrettable) Fashion Trends From the Early '00s

2000s fashion trends

Fashion regrets start here. While we’re all probably growing weary of the ’90s style revival filled with crop tops and chokers, we’re even more uneasy about the possibility of questionable ’00s fashions making an undeserved comeback. 

Now without a doubt, the early ’00s was a weird time for fashion. Not only was all-over denim, surfer-chic, and tacky monogram purses a major thing, but it also was just awkward period filled with regrettable after regrettable style fails (remember denim Britney and Justin?) that we’re all probably second-guessing now.

So, if you’ve blocked out all your regrettable fashion choices you made back then, we don’t blame you at all. But if you are just a tad curious to relive all those crazy fashion memories, here are 15 items you probably had inside your closet. 


Images via eBay

  • UGG Boots


    Image via eBay

    No, we aren’t talking EMU or Bearpaw boots, as every ‘it girl’ back then had to have a pair of these in every single color.

  • Juicy Couture Tracksuits


    Image via ebay.com

    Okay, so maybe you had the Old Navy knockoff version, but every popular princess in your school probably had a pair with the unforgettable Juicy logo on the butt.

  • High Heeled Timberland Boots


    Image vie eBay.com

    Admit it, J.Lo definitely made you buy the Steve Madden version that’s hiding in the back of your closet somewhere.


  • Name Necklaces (a la Carrie Bradshaw)


    Image via eBay

    Eek. Remember all the name tag jokes you would get when wearing one of these bad boys?

    More from The Stir: 20 Cringeworthy Fashion & Style Trends of the '90s 

  • Bucket Hats


    Image via eBay

    Spoiler: Hats were HUGE in the early ’00s! Especially the Kangol kind of ones you regrettably wore for one season. 

  • Trucker Hats


    Image via eBay

    Maybe Von Dutch was out of your price range, but you definitely had one of these with the words "Angel" or "Hottie" written on it.

  • Butterfly Clips


    Image via eBay

    Who else had butterfly-clip-collecting contests with their besties?

  • Tiffany Necklaces


    Image via eBay

    While you probably couldn’t get the same one Reese Witherspoon had in Legally Blonde, the necklace you bought at Claire’s still gave you that cool-girl look.

    More from The Stir: The 14 Most Stylish Moms on Instagram 

  • Chinese Slippers


    Image via eBay

    We’re just going to leave this here. #neveragain

  • Gaucho Pants


    Image via eBay

    Before leggings and yoga pants ruined our lives, we had gauchos, which would give all our classmates major capri envy.

  • Tacky Monogram Purses


    Image via eBay

    When Louis Vuitton Speedys clearly weren’t an option, you improvised and got the next best thing, which, of course, was either a monogrammed Coach or Dooney & Bourke bag.

  • Denim Skirts


    Image via eBay

    You probably had 10 of these skirts, which you proudly wore with those Rocket Dog platform sandals you saved up for.

    More from The Stir: 17 Embarrassing Fashion & Style Trends From the '90s

  • Surfer Necklaces


    Image via eBay

    You didn’t live in California, or even by a beach for that matter. But you still found an opportunity to wear these things like the wannabe O.C. babe you knew you really were.

  • Polo Shirts


    Image via eBay

    And you layered them with tanks and tees like any Abercrombie poster-child of the ’00s.

  • Anything Abercrombie


    Image via eBay

    Seriously though, why did we even bother?!

    More from The Stir: 18 Cringeworthy Fashion Accessories From the '80s

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