Josie Maran

Josie Maran had already landed a cover of Glamour when she became a Guess girl in 1998, but her career only catapulted in the years to follow her Guess campaign when she was signed to a multi-year contract with Maybelline. Since then, she has gone on to launch her own eponymous line of natural cosmetics and has her own character in the video game Need for Speed: Most Wanted. Josie’s early Kate Moss-esque Guess campaign is definitely one of our favs. Fun fact: She apparently was once in a band with Nicole Richie.