Some of her early roles included Dorothy Gale in The Wizard of Oz, Eponine in Les Misérables, Gabriella in High School Musical, and Ariel in The Little Mermaid.
[citation needed] Oakley made her Broadway debut in Wicked at the Gershwin Theatre on January 3, 2012, as one of the show's swings.
[citation needed] Oakley is perhaps best known for her performance in the lead role of Jenna in Waitress, where she originated on the show's first national tour.
[7] Her latest album "THE LIGHT EFFECT" released in June 2022 as a Broadway show, starring Caitlin Kinnunen, Erika Henningsen & Christiani Pitts.
[5] In 2020, Oakley released A Pocket of Time, and donated the proceeds from digital downloads to the Dramatist Guild Foundation for artists who were struggling as a result of the COVID-19 pandemic.