Ready-to-wear clothing is often designed for individuals without disabilities, which can create dressing barriers and challenges for individuals with disabilities, especially those with motor coordination, cognitive challenges sensory and self-regulation issues. In two studies we explored the visions of occupational therapists for the future of dressing through smart clothing and dressing technology. Using co-design and design fiction online workshops, we were able to gather a rich data set that included interview data, virtual sticky notes, creative writing exercises and storyboards. We coded and used thematic and abductive analysis to explore the data and created design fictions to explore the future of dressing technology. Occupational therapists identified challenges that impact dressing tasks, and requirements for the design of technology situated in the near future that would support the autonomy of disabled people.