bailey enrolled in freshman-level courses at the university of alabama in huntsville, and also competed in local beauty pageants. she was the first african american homecoming queen in her high school. after winning the event, she participated in a homecoming queen pageant. even though she did not win, she was contacted by a wilhelmina models talent scout. at age 18, she moved to new york city and signed a five-year contract with the modeling agency. she had raised the money for the move through part-time work at a mall.