This chapter takes an innovative approach to exploring the inextricable relationship between dress, personality, and the self. It starts with a state-of-the-art review of theories and models of the self and personality. Drawing on personality and social psychology, the authors present the theoretical framework that informs their understanding of dress and fashion in relation to the self. They then outline some of the main functions of dress, including physical and psychological protection, communicating information about group membership and different aspects of the self, managing other people’s impressions of oneself, and concealing or camouflaging actual or perceived physical flaws. Using autobiographical memory research, the authors also explore how dress may help maintain a sense of self-continuity, which is beneficial for psychological well-being. They conclude by mapping the functions of dress onto the theories reviewed at the beginning of the chapter. Ultimately, the literature reviewed in this chapter highlights how dress can help express, maintain, and transform the self. It thus identifies one of the key reasons behind the size, power, and success of the fashion industry.