Naomi Sims had an unlikely rise to the top. She came from a troubled home, spent time in foster care and was ostracized by her peers for her height (she was 5'10 by the age of 13). She moved to New York City when she received a scholarship to the Fashion Institute of Technology, and there she attempted to break into the modeling biz. However, racism made it almost impossible. Since agencies often criticized her for having skin that was "too dark," she decided to go straight to the fashion photographers. Gosta Peterson, a New York Times photographer, put her in the 1967 August fashion supplement. Sims used copies of the Times issue as her calling card and soon began landing jobs.

Sims went on to become the first black model on the cover of Ladies' Home Journal and Life magazine and is said to have helped usher in the "Black is Beautiful" movement of the '70s. In 1973 she retired from modeling to start her own multi-million-dollar wig business. Despite her success, her personal style always remained down-to-earth and effortlessly chic. She said: "To always be aware of your face, your figure, to always have to wonder if your hair and nails are perfect -- it's not healthy. Maybe for a few years. Not for a lifetime." Sadly Sims passed away from breast cancer in 2009 at age 61.

In this 1975 photo from a portrait session in New York, Sims models a look that appears straight out of "The Great Gatsby." She paired her 1920s-style cloche hat and pearls with a striped sweater-and-skirt set for a classic ensemble that would totally work for ladies today. Would you try Naomi Sims look?