Nicole Richie, 2007
Just a month after her ex-bestie's stint in the slammer, Nicole Richie was sentenced to four days in jail after she pleaded guilty to driving under the influence. Following in the footsteps of Marilyn and Naomi, Nicole opted for a high-necked LBD when she appeared in court in July 2007. Apparently, it was a good luck charm - she ultimately spent just 82 minutes behind bars.
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