This thesis investigates the gendered dimensions of cosplay and cross-play at Canadian anime conventions. How do cosplayers use cross-play to explore gender identities at anime conventions? What limitations hinder cosplayers from feeling free to explore their identities at these events? Why do cis women and non-binary people assigned female at birth (AFAB) participate in cross-play? I use in-depth interviews with cosplayers, autoethnography, and textual analyses of convention anti-harassment policies to explore these questions. Cross-play at Canadian anime conventions is beneficial to queer, trans, and non-binary attendees as they are able to explore their gender presentations in unique ways. Yet, there are limitations to this freedom, particularly for cis women and non-binary AFAB cosplayers who experience negativity surrounding femininity and heightened sexual harassment. These findings broaden understandings of gender and anime fan practices and encourage convention organizers to update policies on harassment.