Kate Moss

At 5'7", Kate Moss was told she was too short for modeling. She responded by becoming the most photographed woman of the 1990s and single-handedly ending the Amazonian supermodel era with "heroin chic" — a look that was controversial, dangerous, and undeniably epoch-defining. Calvin Klein's Obsession campaign made her a global icon at 18. She's earned an estimated $70 million and survived scandals that would have ended anyone else's career. At 52, she still books campaigns. Moss didn't break the rules of modeling; she replaced them entirely.