Era: 1990s-2000s
Known For: Face of Calvin Klein, Rimmel London and Topshop

While the poster child of heroin chic is a controversial figure, it's undeniable how much she has affected pop culture as a whole. In the 1990s, Moss was an unstoppable force. She ruled over Calvin Klein, dated Johnny Depp, and partied until her heart was content. Nowadays, she's still the Queen of Cool—just peep her Supreme ads.