This chapter takes a positive psychology approach to dress and fashion. It presents and discusses existing literature on how people’s conceptualisation of and relationship with fashion influence their well-being across the lifespan. Well-being is multidimensional and best understood from a holistic perspective. The chapter introduces the different theories of well-being, identifies factors influencing well-being, and discusses well-being in the context of fashion. Using an empirical approach, the authors discuss the different ways in which fashion and clothing can boost psychological well-being on different levels, for instance, mood, emotions, happiness, quality of life, creativity, and relationships with others. In addition, they examine how fashion may enable people to develop a positive self-concept and thrive on a psychological level. Avenues for future research and work in this area are explored. The authors focus particularly on how the fashion industry can further promote positive fashion in terms of how people relate to fashion in their everyday life. They conclude that while the fashion industry has its dark side, the essence of fashion itself can be positive.