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6. Cynthia Rowley

The iconic fashion designer surprisingly got her first big break when she was a high school student and Playboy published a spread of a model in a sailor hat and matching skirt of her design. She couldn’t even show her parents the article. Luckily, after graduation, one of Rowley’s grandmothers gave her $3,000, which she used to launch her first line. Today, Rowley’s fashions are presented bi-annually at New York Fashion Week and sold in signature Cynthia Rowley stores in New York City, Charleston, Chicago, Boston, East Hampton, Japan, Hong Kong and Taiwan, as well as at the company’s web store. Rowley has also partnered with Target, Band-Aid, Roxy and Half Gallery.

stars who got their start in playboy
Everett Collection / shutterstock.com

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