Paris Hilton
A somber socialite trekked to court in hues of gray, white and black to hear her sentence for driving on a suspended license and probation violations. Starting the day with a smart ensemble was good, but it was all downhill from there, as Paris was sentenced to 45 days in jail.
Nicole Richie
On the day she was found guilty of driving under the influence (and later served only 82 minutes), the socialite was definitely innocent of any fashion crimes in this sleeveless Moschino dress and Christian Louboutin heels.
Britney Spears
This groovy geometric dress and killer kicks couldn't do any magic tricks for Britney at a custody hearing in October of 2007. She eventually lost temporary custody of her two sons and didn't regain unsupervised overnight visits with them until June 2008.