Once considered low class or dangerous symbols, tattoos began to be defined as hip, trendy, and glamorous in the 1990s. Using the increasing popularity of tattoos among nineties youth as an example of moral passage, this article examines some of the interpretive processes at work in the destigmatization of deviance. Whereas researchers have positioned political action or population shifts as the main forces influencing moral passage, this article posits a new route toward social change. It builds on participant observation data with a population of middle-class tattooees and examines how individuals attempted to legitimate their tattoos during interactions with others. First-time tattooees in the 1990s are seen as agents caught between multiple symbolic orders—symbolic orders that generated conflicting images of tattoos. Relying on a set of legitimation techniques, middle-class tattooees worked to overcome the negative meanings associated with tattoos by getting body art that conformed to core mainstream norms and values. By examining the creation and use of these legitimation maneuvers, this article reveals the way in which definitions of deviance are negotiated in everyday contexts. In addition, the process of legitimation identified in this article points to one way in which everyday interactions can contribute to larger cultural shifts.