Rolling Style is a research-driven design project that reimagines the wheelchair not only as a functional mobility device but also as an extension of individual identity. Through a co-creative process with wheelchair users, this project introduces a detachable customisation toolkit—an accessory system that allows users to decorate their wheelchairs and make them a part of their daily outfit rather than just the tools that are ignored. The idea emerged from a core insight gathered through in-depth interviews and participatory workshops: many wheelchair users deeply care about the impression they give off to others. However, most wheelchair designs today focus primarily on functionality, often overlooking the importance of self-expression. As a result, wheelchairs tend to look remarkably similar, resembling medical equipment and rarely addressing users’ aesthetic or emotional needs, especially their desire to be seen not as “disabled,” but as stylish and expressive individuals. Digging deeper, the project found that much like fashion, the act of dressing up is not purely about appearance—it serves as a daily ritual of self-affirmation, identity construction, and emotional agency. Drawing on this parallel, Rolling Style applies principles from fashion styling, modularity, personalisation, and outfit coordination to the design of wheelchair add-ons. The final output is a lightweight, interchangeable toolkit that includes attachable modules in various colors, textures, and shapes. These elements can be arranged, swapped, or themed based on the user’s outfit, season, or mood. The project will be presented through physical prototypes, user styling examples, and documentary footage of the co-creation process. It aims to open new conversations in both inclusive design and fashion, inviting us to rethink how design can support not only access, but belonging, agency, and aesthetic dignity.