Lindsay Lohan's recent ensemble escapades in the courthouse, which included an expletive manicure and dangerously low cut blouse, had everyone talking, but the jail bound starlet isn't the first celeb who has gone before the law in questionable couture. While some stars opt to clean up their image when they get a nudge from the judge, others use the courtroom as their own personal runway, and the result can be worthy of a fashion police arrest!

We were beyond shocked in 2005, when Lil' Kim entered the courtroom in startlingly sophisticated style. Famous for cavorting around the stage in pasties and g-string panties, the 29-year-old showed up dressed to impress in gorgeous gabardine suits and cashmere peacoats. However, her rehabilitating style didn't get her off the hook. She was found guilty for perjury and conspiracy and needless to say, when she was released from jail, the Notorious K.I.M returned.