She is best known for playing the role of Ariel in the Disney film The Little Mermaid (2023), which is based on the 1989 animated film of the same name, and previously gained fame as a member of the musical duo Chloe x Halle, along with her sister Chloe, with whom they received five Grammy Award nominations since 2018. Her performance as Skyler Forster on the television sitcom Grown Up earned her a 2020 NAACP Image Awards nomination for Outstanding Supporting Actress in a Comedy Series. Among other things, she played one of the roles in the film adaptation of the Broadway musical The Color Purple (2024). To date, the role of Princess Ariel is the most notable role in Bailey's filmography.