Abstract What can fashion and fashion journalism tell us about the actual and possible representations of disability? Unfolding from a dialogue between the co-authors, this chapter takes a Dutch case study as its starting point to map and interpret how creative professionals responsible for communication in an advocacy organization, as well as journalists and television makers, had great trouble freeing disability from limiting frames of reference. The aim of the chapter is to provide insight and tools for inclusive and reflexive practices of representation. Discourse analysis provides the basis for a multi-layered dialogue. Ingrained, standardized routines in media practice are the problem that the best of intentions cannot break. The Dutch Zonnebloem (Sunflower) organization pointed to a way forward when they invited feedback and engaged in dialogue on their failed media campaign to find funding to design fashionable clothing for wheelchair users.