29 Celebs Who Rocked Super Confusing 2000s Trends

If there's anything I know to be true, it's that the 2000s were a confusing time in fashion. Looking back, it's clear that some of the best-dressed celebrities of today were guilty of establishing some of the strangest trends of the last decade. Six years later, we can laugh about them, but there's no denying they're still confusing. Because, really, how do you explain a patchwork denim dress?

Short answer: you don't. The 2000s were when Von Dutch trucker hats were all the rage, tattoo chokers were an essential part of any ensemble, and those (horribly ugly) popcorn shirts were staples for every It-girl. Don't get me wrong, I'm totally guilty of 2/3 of those trends (I won't tell you which ones, because why would I embarrass myself like that?), but there's no doubt that they're in the past for a reason. Celebs were the biggest culprits when it came to making early '00s trends popular in the first place.

There's no doubt that we've moved on to bigger and better things (although there's no knowing if crop tops and OTK boots will be just as embarrassing in the 2020s). But every once in a while it's nice to see how far we've come. So, here are 13 celebs wearing 2000s trends that establish that the fashion back then was downright confusing.

1. Pink — 2000

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I have no words.

2. Avril Lavigne — 2000

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Best way to describe Avril Lavigne's style back then? Hot Topic plus lip gloss. But seriously, those pants need to be burned.

3. Mandy Moore — 2001

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Considering Moore was only a teenager when this photo was taken, you would think she's be wearing an ensemble that suited her age a little more than a matching denim pantsuit. I guess that's the 2000s for you.

4. Jessica Alba — 2001

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This is why we don't wear cardigans as shirts anymore.

5. Jessica Simpson — 2001


Don't get me wrong, I love denim. But this sparkling denim cape with matching shorts is just too much. Don't worry Jessica, I won't let this 2001 ensemble taint my appreciation for your style.

6. Jennifer Lopez — 2001


Sheer, embroidered mini dresses with baggy sleeves? I have no doubt J. Lo could still rock it, but that doesn't mean she should.

7. Nick Carter — 2001

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Nick Carter, you probably broke a lot of hearts with this spiked hair and faded sunglasses look. But it's not going to work in 2016.

8. Brittany Snow — 2002

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I think this outfit isn't nearly as bad as the others, but even just looking at those shoes makes me cringe.

9. Justin Timberlake — 2002

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Justin. Your shoelace is untied. And that's just one thing that is wrong with this outfit.

10. Anne Hathaway — 2002

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But you're not so lucky, Anne. There are countless things in this outfit that I just simply do not understand. I get that tube tops and drop-waist skirts were a trend back then, but this is not a good look.

11. Nicole Richie & Nicky Hilton — 2002

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What is even going on in this picture? Either Hilton and Richie thought they looked absolutely fabulous in their odd denim ensembles, or they knew they were it was bad and just figured to make the best of it. Either way, it's really bad.

12. Lindsay Lohan — 2003

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You know the now elusive trucker hat had to make it in this list somehow. You do you, Lohan.

13. Christina Aguilera — 2003

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I would love to see someone describe this outfit, because I'm convinced it's impossible. It's that confusing.

14. Beyonce — 2003

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Beyonce obviously looks fabulous, and she's certainly rocking that flowy blazer and light-wash jeans. But let's leave it at that, shall we?

15. Missy Elliot — 2004

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I will say one thing and one thing only: "Work It" Missy Elliot. Even though this ensemble is hard to look at, you do you.

16. Brittany Murphy — 2004

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Considering the trends in the 2000s, this satin gown was a safe choice by the late Brittany Murphy. Even though it didn't stand the test of time, there's no doubt she was drop dead gorgeous it in.

17. Hillary Duff — 2005

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Not going to lie to you, I owned a dress very similar to this one back in 2005. Duff certainly could sell a trend. That doesn't mean it was right, though.

18. Mischa Barton — 2005

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Being a huge O.C. fan, I loved absolutely everything Mischa Barton wore back in the 2000s. Looking back, though, this outfit was already severely outdated for 2005. I forgive you, Marissa.

19. Rihanna — 2005

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Even the style icon herself, Rihanna, wasn't safe from the terrible trends of the 2000s. Clearly, 2005 was a time for vests, jeans, and well, not much else. Either way, I would bet my life that Rihanna would never wear this outfit again.

20. Jay Z — 2006

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Jay's usually got such sleek style. But even he wasn't exempt from the terrible trends of the 2000s. Hint: that pink sweater is not cute.

21. Kelly Clarkson — 2006

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There's no doubt Clarkson can sing. But her 2006 stage wardrobe needed some help.

22. Britney Spears — 2007

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We're all aware that 2007 was a bad year for Britney. But really, Brit. That hat wasn't making it any better.

23. Selena Gomez — 2007

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Ooof, this ensemble is a long call from Gomez's sexy chic style today. I guess you gotta start somewhere!

24. Fergie — 2008


The headband, the belt, the clutch, the shoes, the printed dress... It's too much, Fergie. Wayyyy too much.

25. Khloe Kardashian — 2008

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Khloe Kardashian is easily my favorite Kardashian because of her glamorous bombshell style. So I can't even get mad at this wide leg jean and purse-on-the-shoulder look even though its bad.

26. Kim Kardashian — 2009

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I'm into the revealed bodice of this dress, but the black detailing and the weird asymmetrical top half is just throwing me off. You've come a long way, Kim K.

27. Miley Cyrus — 2009

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A very Hannah Montana-esque look by Hannah Montana herself. It's OK, she's just being Miley.

28. One Direction — 2010

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I bet Harry Styles, Niall Horan, and Louis Tomlison already regret those baggy jeans and sweats. Considering this was before their One Direction fame, though, I guess we can let it slide.

29. Demi Lovato — 2010

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I'm sorry, Demi. I love you and all your self-loving confidence, but this outfit was not a good idea.

I think it's safe to say the 2000s were a rough decade for fashion. And while I gave my best attempt at explaining it, there are really no words for the above looks, and so many more, from the 2000s. Let's have a moment of silence for the death of all of those terrible trends, and a hallelujah that they're gone!