Cleveland studied at New York’s High School of Art and Design, where her first love was fashion. By her early teens, she was designing and wearing her own creations. Her modelling career began by accident in 1967 when she was spotted on a New York subway by Carrie Donovan, an assistant editor at Vogue. The 14-year-old was on her way to classes at LaGuardia Performing Arts School when, “This assistant followed me,” Cleveland recalled. “My girlfriend said, ‘You better run. There’s a dyke chasing you’. I said, ‘What’s a dyke?’”
After working with Ebony, Cleveland began to attract the attention of the major fashion designers of the day, working first with famous names such as Jacques Tiffeau and Stephen Burrows. Soon she was meeting and working with all of fashion’s top playmakers, including Diana Vreeland, Irving Penn and Andy Warhol. But despite her early success Cleveland grew disillusioned with America and its racist attitudes towards black models. One day, fashion illustrator Antonio Lopez invited her to try her luck in Milan and Paris instead.
Cleveland returned to United States in 1974 (the year of US Vogue’s first black cover model), and continued modelling into the 1980s. She went into semi-retirement after getting married and giving birth to two children, Anna and Noel. Today she still makes intermittent appearances on television and on the runway.