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The 32 Most WTF Celebrity Outfits From The '00s

What were they thinking?

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1. Alicia Keys – February 2003

Adam Rountree / Getty Images

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!"


7. Mariah Carey – February 2003

Steve Schaefer / Getty Images

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."


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

Brenda Chase / Getty Images

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


17. Kanye West and Anastasia – November 2004

Carlo Allegri / Getty Images

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

David Mcnew / Getty Images

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."

20. Kelly Osborne – May 2003

Robert Mora / Getty Images

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

Kevin Winter / Getty Images

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."


29. Britney Spears – November 2000

Vince Bucci / Getty Images

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

Chris Weeks / Getty Images

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."