20. Kathy Ireland – 1988
Kathy Ireland
Kathy Ireland is one of the richest models now who started her career while still in high school (1979). Her career was slowly growing strong when it finally hit the top mark in 1989 when she graced the cover of the 1989 Sports Illustrated Swimsuit Cover Issue. Interestingly, this issue copped the best-seller title as it was voted the “Greatest Sports Illustrated Swimsuit Cover” of all time while it celebrated its 50th anniversary. She is an entrepreneur and founder of a marketing agency known as Kathy Ireland WorldWide (1993). As of 2015, Forbes recorded her net worth to be approximately $420 million.
21. Linda Evangelista – 1990
Linda Evangelista
Linda started her modeling career with Elite Model Management in 1984. As she progressed in her newfound passion, she was influenced by her photographer Peter Lindbergh to cut her hair in a style called Linda. Interestingly, he worked in her favor and gave her much success as a lot of women around the world found inspiration in her new look and replicated the style. Her modeling nickname was Chameleon, as she was able to change her appearance to appetize the camera. She was voted the “Greatest Supermodel of All Time” through the TV show Fashion File in 2008.
