The purpose of this thesis is to highlight and showcase all aspects of the costume design process involved in the San Diego Asian American Repertory Theatre's (SDAART) production of Henry D. Hwang's 2002 revival of Flower Drum Song at the La Jolla Playhouse, Adele Shank Theater, San Diego, California in May of 2011. The original 1958 musical is a Rodgers and Hammerstein film and theatrical production based on the novel the Flower Drum Song written by C.Y. Lee. Designing this project required detailed research of 1960's Chinese-American culture and events in San Francisco, California, along with the Mainland Chinese experiences of this period. The project entailed close collaboration with director Peter Cirino and fellow designers, development of a visual concept and costume construction, and culminated in the production itself. This thesis features the problems encountered and the solutions I implemented in order to accomplish a successful outcome in communicating the essence of characters at a cultural crossroad that resulted in a well-received play.