Year Arrested: 2002

Crime: Drunken driving.

Before his arrest that night in 2002, Nick Nolte was partying, and what says party animal like a bright, floral Hawaiian shirt?  The boxy cut of the shirt is the classic shape of vintage Hawaiian shirts, and the uneven collar is just the touch of sprezzatura that Nolte needed to finish off this outfit. Florals have made a big splash recently, but Nolte was a decade ahead of the curve.