This thesis builds a picture of the inner workings of fancy dress as a form of adult socialization, individual expression and material practice. It uses ethnographic methodologies to study one particular group of regular fancy dress practitioners, a Sydney-based group of Baby Boomers friends of which I am a member. This group is worthy of study because they have participated in fancy dress parties for over thirty years and these events have been integral to building, shaping and sustaining their community. The thesis proceeds from the finding that the purpose of wearing fancy dress at parties is to draw people together in playful and shared celebration. It investigates the complexities of adult fancy dress manifests as a conduit for community entertainment and social cohesion. It also explores what being in a fancy dress costume brings to an event as well as exploring what is involved in its preparation and execution. Fancy dress is also a dress code that is part of the continuum of clothing and fashion etiquette that has boundaries of expectation and acceptance. Fancy dress practice is complex because it encompasses the meaning and production of fashion and dress, the hierarchies of appearance and gender, the performance of self and challenges our notions of the appropriately dressed body. The conclusion examines the role of dress- up as a popular form of social celebration in the broader community and points the way for further study.