This is an extensive survey of early saints’ lives that involve the motif of a woman crossdressing and passing as a man, generally in order to participate in a monastic community at a time when there were no women’s communities available. Given that the context is hagiographical, this activity is framed positively, not only in pragmatic terms (it enables the woman to do something holy) but due to the greater value placed on men, especially in the context of religious practice.