Though there is a vast literature on performances of drag, performances of gender and sexual transgressions outside of drag clubs are less studied. This case study of men’s marches protesting violence against women—“Walk a Mile in Her Shoes” marches— examines the politics of such transgressions. Cross-dressing to various degrees is strategically utilized at these events in an attempt to encourage men to become empathetic allies. This article suggests, however, that context is critical to the political potential of performances of drag. (...) The author’s observations of the interactions at the marches suggest that drag at “Walk a Mile” marches often symbolically reproduces gender and sexual inequality despite good intentions. At these marches, feminism is gendered when performances of politics and protest are contextually framed as gender and/or sexual transgressions when “feminism” is understood as “feminine.”. (shrink)