29 Photos of Celebs in Early 2000s Grammys Fashion That Will Keep You Up At Night

Christina Aguilera went through a lot of fashion phases in the beginning of this century

By Jenna Mullins Feb 05, 2015 7:58 PMTags
Early 2000s Fashion, GrammysGetty Images

Ah, the early 2000s. What a time for fashion! Of course, now that we've evolved and have stopped wearing as much pleather as we used to, these photos might give you nightmares and restless nights for the next week or so.

And since the Grammys are coming up faster than the type of thong celebs used to wear with their low-rise jeans (what's the point of low-rise jeans if you can't see the thong, right?!), we thought we would journey back to a time when stars would hit the red carpet in outfits that were glorious in their tackiness. Because when it comes to the early aughts, didn't we all make horrible fashion mistakes? Celebs...they're just like us!

1. Britney Spears (2000)

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Britney's first Grammys! She looks so pure and regal.

2. Destiny's Child (2000)

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R.I.P the second original crew of Destiny's Child.

3. Aaron Carter (2000)

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His tux says formal, but his stance says "'Sup?"

4. Penelope Cruz (2005)

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Everyone was bit by the fedora bug in the early '00s. 

5. Rachael Leigh Cook, Tara Reid and Rosario Dawson (2001)

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Josie and the Pussycats was an underrated movie!

6. Sisqo (2000)

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No would could rock head-to-toe shiny red like this man. Although we believe that the sun around the belly button tattoo trend was more of a female thing, but hey, whatever makes your booty go...

7. Christina Aguilera (2001)

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That hair just looks like it hurts her scalp.

8. Sheryl Crow (2005)

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For when you want to show some skin, but in a ladylike way, just show most of your torso. Also, this is just like the dress Casey wore to prom on Laguna Beach, right?!

9. Kanye West (2004)

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Kanye just rockin' that salmon and khaki.

10. Traci Bingham (2001)

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We feel like she's trying to draw attention to something...but we can't quite figure out what that something is.

11. Shannon Elizabeth (2000)

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Who OK'd this bandanna?!

12. Gretchen Wilson (2005)

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We would mock this red blue carpet look, but we were all guilty of the flare jeans with pointy heels at one point or another in the 2000s.

13. Jane Krakowski (2000)

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Jenna Maroney is better than this. In fact, we need a little big of a palate cleanser after this one:


14. Avril Lavigne (2003)

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Sadly, this would not be the last time people frowned upon Avril's life choices.

15. Britney Spears (2002)

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Those curls made her closer to heaven, from where she had recently fallen.

16. Brad Paisley (2001)

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It takes a bold man to show up to an award show in a royal blue suit with flames on it.

17. Faith Hill and Tim McGraw (2000)

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Remember shrugs, you guys?! The go-to item for when you just barely wanted to cover your shoulders and upper back.

18. Christina Aguilera (2004)

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Who says fringe, glitter and fur doesn't mix?

19. Beyoncé (2004)

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Behold! Solo Beyoncé hitting the Grammys with a confusing hairstyle.

20. 'N Sync (2000)

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Where do you look first?! Joey Fatone's hair? Lance Bass' jacket? Justin Timberlake's mustard-green ensemble? His suit looks like the couch most parents have in their basements that they later pass on down to their kids whenever they move out of the house and get their first apartment.

21. Maroon 5 (2005)

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Ladies and gents, Sexiest Man Alive Adam Levine!

22. Sheryl Crow (2000)

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We don't have anything to say about this outfit. Because really...what can you say?

23. Christina Aguilera (2000)

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Remember when it was considered a huge upset that Christina won Best New Artist over Britney Spears? Those were the good ol' days.

24. Jennifer Love Hewitt (2004)

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Make no mistake about it, she's wearing see-through shoes.

25. Haylie and Hilary Duff (2004)

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Check out the Duff sisters looking like icy pink teenage dreams.

26. Fergie (2005)

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Nothing says "sexy early 2000s" like baggy, plaid capri pants.

27. Britney Spears (2000)

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Britney was all about iridescent fabric at this Pre-Grammy party. She sheer fabric. And fur. And rhinestones. And her midriff.

28. Alicia Keys


It kind of looks like someone forgot to make the front of the dress and Alicia was just like, "screw it, I'll wear it with jeans." And...is that a denim bracelet?!

29. Pink, Christina Aguilera and Mya (2002)

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These gals just came from performing "Lady Marmalade" (we hope), so we will forgive them for what's going on here. However, we just want to point out that Christina kind of looks like she's wearing a diaper.