Simon has been at the forefront of 'colour-blind casting', playing roles traditionally taken by white actresses. From the mid-1980s to the late 1990s, a time when it was unusual for black women to feature as leads in leading Shakespeare plays, Simon played several major roles for the RSC. Her first leading role, and the first for a black actress at the RSC, was as Rosaline, in Love's Labour's Lost, directed by Barry Kyle, in 1984. Jami Rogers, in her book British Black and Asian Shakespeareans (2022) commented that in Kyle's production, where the women were dressed in Belle Époque-style silk dresses, Rosaline's clothing "immediately marked her as a woman of high status ...For the first time on a major British stage, an African-Caribbean woman portrayed an intelligent, witty and strong leading Shakespearean character." Rogers described the reviews of the production as "glowing". She noted that some reviewers and academics "treated Josette Simon's casting ... as a novelty", criticising the description of integrated casting as an "experiment" as "deeply problematic as it infers the practice is an aberration rather than what it was [by 1990], a common practice".
