5’10 Alabama-born supermodel Cynthia Bailey moved to New York City 25 years ago to pursue a career as a fashion model. With nothing more than a high school Homecoming Queen crown and a few local beauty pageants under her belt, she knew that she had arrived when Wilhelmina Models in New York City jumped at the chance to sign her to a 5 year contract. From there things really started to take off! Her first booking was for the cover of ESSENCE magazine which not only was one of the highest-selling covers in ESSENCE history, and was also a personal favorite of then editor-in-chief Susan Taylor. It wasn’t long before Cynthia would find herself gracing the cover of ESSENCE magazine again for the second time which literally flew off the newsstands!