Designing technologies that clothe, adorn, or are otherwise placed on the body raises questions concerning the role they will play in dressing ourselves. We situate self-fashioning - or the process through which we stylise and present our bodies - as a complex practice where a series of social, material, and contextual factors shape how we present ourselves. Informed by reflective discussions and projective design tools, we contribute three critical points of departure for self-fashioning technologies: (i) Purposeful examining discomfort as an ongoing phenomenon, (ii) Supporting mimesis and visibility as qualities to be negotiated, and (iii) Envisioning the multiplicity of the body. We call for the design community to help devise fashionable technologies that are sensitive, caring, and responsive to the complexities of fashioning our bodies.