Well, now you can find out! Thanks to MTV and Cotton, who've joined forces to create a series of Webisodes where celebs play their own worst critics (as if they don't have enough already).
"What Were U Thinking" features stars talking about five of their best -- and worst -- looks. Kelly Osbourne kicks off the new series, and as you might imagine, she's got some pretty amazing insight into some of her wild and wacky style choices. Brilliant!
We can't wait to see who's up next. We're not going to lie -- our fingers are crossed for Bai Ling.
Watch Osbourne's Webisode below and let us know in a comment who you'd like to see reflect on his/her own style: the good, the bad and the ugly.