This article has emerged from a research partnership between Filipino activists and an academic researcher and ally. In this discussion, we explore a unique arts-based feminist popular education project that used the format of a fashion show (not usually associated with women's emancipation) to tell stories about the colonization of the Philippines, its history and present neo-colonial realities, and the relationship between this history and Filipino women's exploitation. In 2004, 2005, and 2008, the Philippine Women's Centre of British Columbia (PWCBC), one of the longest-standing feminist organizations in Vancouver, created and launched three political fashion shows. Framed by feminist perspectives of transnationalism and global capitalism, as well as feminist approaches to popular education, we dialogue about three scenes/dresses from these shows, selected as examples of the power of visual and performative art to tell about, wear, and learn about colonial history and neo-colonial realities. We conclude that the political fashion shows of the PWCBC created spaces of public pedagogy and feminist empowerment and praxis.