after working as a runway model in paris and milan for a year, bailey returned to new york city and modeled for maybelline, oil of olay, and target and in magazines including "vogue", "glamour", "elle", and "vanity fair". she appeared on two "essence" magazine covers in june 1995her first job as a modeland 1997. the magazine's then editor-in-chief susan l. taylor described bailey as one of her favorite models. bailey's favorite modeling job was a "vanity cover" shot by annie leibovitz and featuring iman, beverly johnson, naomi campbell, and tyra banks; iman had invited bailey to participate in the shoot.