Once Upon a Mattress is a great work in the American musical theatre cannon that is often produced but seldom reinterpreted. Mirroring the zeitgeist of the Mid-century world, this show’s characters display common stereotypes of the era. This production latched onto these tropes and reimagined the familiar musical in the library of a Mid-century high school–a location to which these stereotypes are often associated. Two worlds were to be represented: “The Library” and “The Kingdom”. Each character’s costume was designed to represent a trope in both worlds, with academic motifs painted in the seams. These caricaturised designs allowed the Director and Performers to draw on and subvert audience expectations–thereby embodying the satirical nature of the show.