The aim of this special issue is to enable a dialogue between masculinity studies and transgender studies and attempt to find common areas of inquiry and mutual knowledge production in such conventionally divided arenas. The contributions to the issue explore a multiplicity of masculinities, which are seen as situational positions that can be deployed and activated by a variety of bodies, and in this way attempt to de-essentialize masculinity as grounded in a cis-male body. In this introduction, we discuss how masculinity studies have approached transgender issues, its general lack of interest in trans masculinities, as well as how transgender studies have related to masculinity theorizing.