Brand: Roberto Cavalli

Roberto Cavalli found success early on by patenting a leather printing technique that caught the attention of Hermès and Pierre Cardin. In 1970, at age 30, Cavalli launched his eponymous brand that still sells extravagent clothing today, and Cavalli is still dressing like he wishes he was 30. Instead of re-capturing some young go-hard magic with his all-black ensembles, Cavalli looks like that old dude steady lurkin' in the club who makes wary girls keep one hand over their drinks when he's prowling nearby.