Fashion and philanthropy, both the study and the practice, at times converge. It is at this intersection, conceptualized as the social world of fashionthropy, that this research takes place. A literature review on the history of fashion and philanthropic studies is presented as well as a conceptual framework based on Georg Simmel’s notion of fashion’s dualism and Gates’s view that a binary motive is the best fuel for market- driven philanthropy. This paper then explores concepts of capitalism, social responsibility and social worlds through an interpretivist lens in relation to three Canadian case studies on fashion and philanthropic happenings in Toronto.