In this thesis, I argue that medieval people in Latin Europe had complex, overlapping identities and experiences of gender and sexuality that developed in their specific temporal and geographical contexts. The internal understandings of identities and the external expressions and interpretations of such identities are sites of historical possibility—and sources of potential inter-and intra-personal conflicts Medieval writings like Le Roman de Silence demonstrate how these identities could be constructed and expressed for literary and rhetorical purposes. Extant court cases, including those of John/Eleanor Rykener, Vitoria of Lisbon, and Katherina Hetzeldorfer, demonstrate the complexity of lived experiences of identity, and how deviation from accepted community and cultural norms could prove dangerous. It is impossible to assert such identities of gender and sexuality for historical figures of the medieval era with complete certainty, but the exploration of these identities is necessary for a fuller understanding and representation of the period and the people who lived throughout it.