Clothingdisability not onlyfashion inclusion supports the individual’s physical comfort and protection needs but also, when considering fashion, plays a powerful role in one’s sense of self. For many disabled people, however, adequate clothing choice remains limited. The resulting unmet psychological, social, or functional needs can negatively impact their well-being. This chapter explores the complex intersection of psychology, fashion practice, and adaptive apparel research to understand garment-related, retail, and representation barriers to broader fashion inclusion, as well as the possible impact of this exclusion on the self-esteem and self-perception of people with disabilities. After discussing how potential discrimination or constructions of difference around disability may influence fashion inclusion, further research is explored on how a healthy self-image and self-empowerment for disabled people can be fostered through fashionable and comfortable adaptive apparel, empathic design practices, and authentic representations. Future research recommendations are finally discussed for the role that psychology can play (e.g., managing ethics in inclusive design projects, using fashion creativity as therapy) in supporting more meaningful and comprehensive fashion inclusion that considers the well-being of diverse individuals with disabilities.