Motivated by studies of dress and the importance that it has on identity formation and expression of self, this research tries to answer the question of how can an interactive tool create greater means for self-expression of the dressed body through the design of textiles? The goal of pursuing the question is to ultimately promote a more sustainable fashion culture that relies on the creation of long-lasting products. Employing Research through Design as the main methodology, this research went through a series of sequential design experiments – namely workshops and prototypes – with the ambition of generating knowledge in the context of the design space, and in order to inform the design of the interactive tool proposed by the research question. The main research findings suggest that the direct engagement with the painting of textiles through ruled self-reflection tasks, in collaboration with a machine, provides great means for the creation of long-lasting products – showing, therefore, a fruitful path towards fashion sustainability. In addition to the conception and building of a final artifact, this research resulted in a set of guidelines that aims at advising the creation of other future artifacts.