21 Pieces Of Cringe-worthy Style From The 2000’s


Oh the millennium decade.  It was the best of times and the worst of times.  The economy was great, fashion was at an all-time low and people had no clue how to dress.  We love the shocking nostalgia that comes to us when we analyze the outfits we allowed ourselves to wear back then.  Sigh.  Here are 21 pieces of cringe-worthy style from the 2000’s.

1. It was a time when things were way too tight and short

After Jessica Simpson starred in the remake of Dukes of Hazzard, heels with short-shorts and tight tops were back in style.  Too bad this look is only pulled off by people who look just like Jessica Simpson.



2. Abercrombie sold skirts like this

That doesn’t look long enough to be a top, let alone a skirt.  And what is with that ruffle action?

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3. Metal-clasp bracelets were all the rage

Everyone had one of these.  Usually girls would put a charm or two on them and you could use them to knock someone out if you got in a fight.

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4. It was all about the designer jeans

Designer jeans were ridiculously expensive and usually stretched out by the end of the day, thus needing to be washed before they could be worn again.  Ugh.

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5. Swarovski crystals were a hit

You wore as many of these as you could handle.  Seeing them now, I just want to  chuck them.

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6. T-shirts had the cut-off look

All your t-shirts looked as if someone took some scissors to the neck before putting them on the rack.

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7. Whatever this was…it was gross

This was a common look in the 2000’s by girls bending down to pick up a pencil or tie their shoe.  Gross. Trashy.  No, just no.

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8. Baseball-style shirts

Everyone had one of these.  Most of them didn’t fit half as well as Paris’ here. 

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9. Long drapey sweater things

Not the flowy comfy sweaters that are all big and nice that people wear now.  These things looked like a sweater dress gone wrong.

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10. Henleys

The 2000’s was the decade of the henley, particularly striped ones.  May they rest in peace.

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11. Tight polo shirts

EVERYONE wore polo shirts (girls and guys) and the tighter you wore it, the better you wore it.

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12. Ugh…. Ugg boots

These boots are ugly and only functional if you live somewhere that’s very snowy but they were a total fashion statement nonetheless.

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13. Name necklaces

Thank you very much, Carrie from Sex and the City.  This one was all your fault.

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14. These awful terry cloth dresses

This did not look good on anyone.  Especially if you wore it with platform foam flip-flops.  Ugh, I’m gagging already.

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15. Doo-rags for non-hood rats

Either you looked like a thug wannabe or a pioneer girl sporting one of these on your head.

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16. Multiple hairstyles at once

Curly, crimped or straight?  Take your pick and stick with it.

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17. Flag wear

It is not appropriate or fashionable to wear a dress made to look like the flag, unless you are a member of the Spice Girls. 


18. Angsty singers

Britney was not that hardcore, Jessica is rocking the off-the-shoulder look that was so popular back then and Avril was all about looking emo and punk and people loved it.


19. This Brittany Murphy ensemble

We sure that if she were still alive today, her fashion sense would be totally on pointe, like Drew Barrymore. 



20. Von Dutch hats

Whose idea was it to wear trucker hats and make it a thing?  Because they should die.

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21. This no-no outfit by Ashlee Simpson

Boots with gaucho pants and an unnecessary scarf?  No, no, no. Thankfully, she’d never make this mistake nowadays.