So, we were all set to name Madonna the Worst Dressed of the Night at the 2009 Costume Institute Gala. Then we spotted Leighton Meester. Oh mah holy hell. And the sad thing is, Leighton could just have escaped arrest here, if she'd just stopped at the dress. If she'd somehow managed to resist pulling on those leggings and creating this clashy-mcclash of an outfit, she could have been spared. As it is, she's now sitting in the back of the cop car, along with Madonna. We know you probably wanted to escape Blair Waldorf for the night, Leighton, and we admire you for that, but sorry: you're cuffed.
Celebrity Fashion, Met Costume Institute Gala