31. Ellen DeGeneres
Ellen’s style has not changed in 10 years and she is all the better for it.
30. David Spade
Guys are still kind of dressing like this, so good for you David Spade. I guess.
29. Queen Latifah
Aw, QL looks really cute here.
28. Amanda Bynes
I think seeing Amanda Bynes look slightly normal — even when dressed like Regina George — feels like a relief. So this isn’t all so bad.
27. Ashley Olsen
I’ll forgive the sateen wide-leg trousers because her hair looks pretty classy.
26. Lindsay Lohan
Old skool LiLo <3
25. Bow Wow
It was at this point that Bow Wow appropriately dropped the “Lil” from his name, as reflected in his pants, sized XXXL. I can’t say that I particularly endorse Mr. Wow’s ensemble here, however variations of this style can still be seen today, which I guess would classify this outfit as a classic. Sadly.
24. Frankie Muniz
The Malcolm in the Middle star chose to epitomize the average 2000s dude. This outfit could have been worse.
23. Benjamin McKenzie
Hello. I still like you.
22. Hugh Jackman
I hate to say it, but the men are basically winning this ranking.
21. Sleepy Brown
Aside from the glasses, there’s nothing super duper horribly wrong with this outfit.
20. Jennifer Love Hewitt
A memory of a time when JLH was still relevant and really into flared jeans.
19. Alexa Vega
Remember this girl? From Spy Kids? If I had to choose any of these outfits, I guess I’d feel the least shame in a rainbow tube top and cargo pants. I think. I’m not sure.
18. Jennifer Lopez
Despite wearing an outfit that is downright insane, J. Lo just basically gets away with anything and it feels kind of wrong to diss her.
17. Drake & Josh
Here, Drake and Josh perfect the Aging Rocker Still Hanging On and Anime Nerd Hoping To Get Laid looks, respectively.
16. Nick Cannon
This outfit, inspired by traffic cones, makes me feel nothing.
15. Jennifer Garner
True Religion jeans. Kitten heels. I don’t even know.
14. Miranda Cosgrove
She’s so wee! Those are totally the definition of tween jeans.
13. Paula Abdul
This entire outfit is drunk.
12. Jim Carrey
In Tron casualwear. I think.
11. Mary-Kate Olsen
Using basic black as a canvas, Mary-Kate chose to embellish with mismatched accessories. It’s not the worst thing I’ve ever seen, but the girl is just so gosh darn skinny = not a good look.
10. Cameron Diaz
Sort of like a lampshade went to Free People.
9. Mischa Barton
Remember the time everyone wore ice skater outfits over boot cut jeans?
8. Randy Jackson
My dad is still wearing this shirt.
7. Giovonnie Samuels
Here, Giovonnie Samuels of The Suite Life of Zack & Cody … I have been sitting here for 10 minutes trying to explain how I feel about this. And I simply cannot.
6. Lacey Chabert
I want to burn this.
5. Anne Hathaway
Same with this one.
4. Avril Lavigne
Wearing approximately everything from Hot Topic. And are those convertible cargo pants?
3. Jamie Lynn Spears
Looking sort of like she’d played dress-up, except the sizes were all correct.
2. Adam Sandler
I find this shirt to be highly depressing.
1. Raven Symone
It’s like a Princess Jasmine meets cigarette girl mashup … purchased from Pier 1.