The 32 Most WTF Celebrity Outfits From The '00s

What were they thinking?

1. Alicia Keys – February 2003

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What was she thinking? "Ponchos are cool, hats are cool, scarfs are cool, beige is cool, casual is cool. OMG a casual beige, striped, hooded poncho – PERFECT!"

2. P!nk – September 2000

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What was she thinking? "I know, I'll cut the waistband off my jeans – that will simplify this outfit."

3. P!nk – August 2002

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What was she thinking? "I wonder what I would look like with loads of tattoos... Wait, I have a Sharpie!"

4. Jennifer Lopez – February 2003

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What was she thinking? "I want to look peasant chic, but also I want people to know where my nipples are."

5. Victoria and David Beckham – May 2003

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What were they thinking? "White is so elegant, so classy, so understated. And so are corsets and diamantes."

6. Mel B – April 2001

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What were THEY thinking? "Push for freedom, push, push, FREE THE NIPPLES!"

7. Mariah Carey – February 2003

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What was she thinking? "I'm doing a basketball concert, so I'll wear a basketball-themed dress, and then everyone will know I care about basketball at the basketball concert, because basketball."

8. Christina Aguilera – April 2001

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What was she thinking? "This velvet dress is mighty sweaty. I know if I just cut a little ventilation hole here – wow, this is so much fun!"

9. Christina Aguilera – August 2002

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What was she thinking? "Tops are sooo 1999."

10. Madonna – December 2005

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What was she thinking?

"A whole new world

A new fantastic point of view

No one to tell us no or where to go

Or say we're only dreaming..."

11. Madonna – November 2005

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What was she thinking? "So glad I'm wearing this belt, otherwise my knickers would be 'round my ankles!"

12. Lil' Kim – August 2001

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What was she thinking? "I'm loving my look but it needs MORE. Maybe just a couple of gold spray-paint stripes on these boots. There, perfection!"

13. Lil' Kim – September 1999 (sorry, but had to include)

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What was she thinking? "I LOVE my left boob, but HATE my right boob, so this lilac shiny mermaidy jumpsuit is just perfect."

14. Lil' Kim – October 2003

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What was she thinking? "I LOVE my left leg, but HATE my right leg, so this finishing-flag-themed, Impressionistic dress is perfect!"

15. Paris Hilton – January 2001

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What was she thinking? "Always use the same animal to make your halter tops and cuffs. That's hot."

16. Paris Hilton – April 2003

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What was she thinking? "Duvet jackets are hot, pink is hot, silver eyeshadow is hot. Wearing your trainers properly is NOT HOT."

17. Kanye West and Anastasia – November 2004

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What was she thinking? "Bitch stole my colour scheme."

What was he thinking? "You know whose style is underappreciated? Geography teachers, and dads on golf holidays!"

18. Destiny's Child – February 2001

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What were they thinking? "I'm so glad our Austrian ex-nun nanny made us these outfits from those old curtains. I don't know how we could have done it without her. DOE, A DEAR, A FEMALE DEAR."

19. Destiny's Child – September 2001

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What were they thinking? "Forget the sound of music, it's allll about the colours of the wind these days."

20. Kelly Osborne – May 2003

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What was she thinking? "I really want to wear my new raggedy blazer, but it's a bit chilly – I'll just wear my hoody underneath, no one will notice."

21. Kelly Osbourne – June 2002

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What was she thinking? "In years to come people will notice that my pinstripes are actually made up of my name written again and again, and then they'll notice that my undone bow tie matches, and they'll think, 2002 was really her year."

22. Avril Lavigne – August 2003

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What was she thinking? "I'll wear pink because I'm a girl and black because NO ONE UNDERSTANDS ME."

23. Gwen Stefani – October 2001

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What was she thinking? "I'll wear cropped trousers and fishnets to the Vogue awards – they'll never go out of style."

24. Gwen Stefani – December 2001

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What was she thinking? "Cropped trousers and fishnets are such a classic, timeless look."

25. Fergie – November 2003

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What was she thinking? "Always match your heels and your bum bag, and never roll your dungarees all the way up."

26. Anastasia – February 2002

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What was she thinking? "The earrings would have been too much."

27. The Sugababes, but Mainly Heidi – February 2004

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What was she thinking? "I think my fly might be undone, but if I check now the paps will get me."

28. Justin Timberlake – July 2000

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What was he thinking? "The way my fingerless gloves match my bandana really pulls this outfit together."

29. Britney Spears – November 2000

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What was she thinking? "I don't think anyone can see the stains on this dress. It's really not that obvious that I spilt a whole jug of coffee down my front."

30. Britney Spears – December 2000

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What was she thinking? "This tie-dye-hat-and-coat combo is so hip, but I'd really like to show off some flesh, so I'll just wear my shiny bikini underneath it."

31. Britney Spears – February 2003

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What was she thinking? "It's kind of chilly out, but I have killer abs right now, PASS ME THE SCISSORS."

32. Britney Spears and Justin Timberlake – January 2001

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What were they thinking? "Smart casual is just such a confusing dress code."