1. This week, everyone’s favorite punk princess Kelly Osbourne talks about her best and worst fashion moments and why she doesn’t "give a &$^% if you like what she’s wearing or not!"

More On Kelly's Style

  1. Kelly talks about what she's wearing today and warns of the dangers of shopping while stoned!

  2. Check out a look from Kelly's past that had her feeling extra beautiful!

  1. From Little Punk to London Diva, see how Kelly's style has evolved in our WWUT photo recap!

  2. Watch Kelly's fav London designer chat about the style of her long-time fan.

  1. Can you tell when Kelly's wearing a wig? Take the quiz and test your skills!

  2. Find out more on which designers Kelly backs and where to get her statement-making look for less!

  1. Check out videos, photos and more from French band, Phoenix.

  2. Check out Kelly's music videos, lyrics from your fav albums, photo flipbooks and more!

About Kelly Osbourne

What would happen if we took your favorite fashionable celebs, showed them five outfits they've worn out in public over the years, and asked them, "What Were U Thinking?" You're about to find out!

This week we’re talking to controversial fashion icon Kelly Osbourne, reality television star, recording artist and and author of the forthcoming book Fierce, an advice memoir for girls under 21.

Kelly Osbourne captured our attention when she first appeared with her family on the smash hit MTV reality show The Osbournes in 2002. Foul-mouthed and frequently flipping off her ultra-famous rocker dad Ozzy Osbourne, mom (and Dad's manager) Sharon and brother Jack, Kelly endeared herself to millions of rebellious teenagers looking for inspiration. Once famous for being herself, Kelly also made a name for herself as a fashion rebel by showing up on red carpets with shocking pink spiked hair, crazy punk outfits and giving the finger to photographers -- sort of like a baby Courtney Love. Unfortunately, most of the time, Kelly's outfits landed her on worst-dressed lists, with nasty fashion critics calling her fat, ugly and a mess week after week. It wasn't the easiest thing for a 16-year-old to handle, and Kelly took it to heart in the worst way possible: she became addicted to prescription painkillers. According to Kelly, "I found, when I take this, people like me. I'm having fun, I'm not getting picked on. It became a confidence thing."

Though Kelly continued to battle addiction over the next few years, the thing that really turned the tide was a 2005 move back to her native London. Finally free of her parents influence and the Los Angeles paparazzi, Kelly sought treatment for her drug problems. And as she got sober and grew older, she became a student of fashion, befriending London designers and studying the great designers of the past for inspiration. Kelly lost some weight naturally and when she showed up at the Pride of Britain awards in 2005 in a stunning red Vivienne Westwood dress, she knew it was a turning point in the public perception of her fashion sense and her life.

Since then, Kelly has taken her rebellious punk roots and married them to the high fashion influences she surrounds herself with in London. Her three favorite designers are Givenchy, Karl Lagerfeld, and Hannah Marshall and she's hooked on the new shoulder pad craze sweeping the catwalks. All grown up now, engaged to super hot model Luke Worrall and wearing only the top designers when she goes out, Kelly finally says she truly "doesn’t give a @#$% what anyone thinks." And that's what makes Kelly Osbourne a true fashion icon.

Past Guests

  1. We asked Jessica Szohr 'What Were U Thinking?' on October 21. Watch the episode now!

  2. We asked Ashley Greene 'What Were U Thinking?' on October 12. Watch the episode now!

  3. We asked Nelly Furtado 'What Were U Thinking?' on September 28. Watch the episode now!

  4. We asked Kim Kardashian 'What Were U Thinking?' on September 21. Watch the episode now!

  5. We asked Kristin Cavallari 'What Were U Thinking?' on September 9. Watch the episode now!

  6. We asked Keri Hilson 'What Were U Thinking?' on August 24. Watch the episode now!

  7. We asked Adrienne Bailon 'What Were U Thinking?' on August 10. Watch the episode now!