Kate Moss

At 5'7", Kate Moss was told she was too short for modeling, yet she became the most photographed woman of the 1990s and ended the Amazonian supermodel era with 'heroin chic'—a look that was controversial but epoch-defining. Calvin Klein's Obsession campaign made her a global icon at 18, and she earned $70 million, which is 40% less than #3 Beverly Johnson's estimated wealth but driven by longer brand longevity. Moss survived scandals that would have ended any other career—she is the only supermodel to return to top campaigns after a drug controversy. At 52, she still books campaigns, outperforming the average model's career span by 20 years. Moss didn't just break rules; she replaced the entire system, blazing a path for shorter models to dominate.