This dissertation presents a close reading of the Life of St Matrona, a mid-6th century hagiographic work about a 5th century monastic who founded a monastery in Constantinople for persons assigned female at birth who desired to dress as men. In response to recent scholarship categorizing cross-dressing saints either as queer or as straightforwardly women, this dissertation presents an argument for reading the Life of St Matrona as a trans narrative. To articulate a trans hermeneutic for reading pre-modern texts, this dissertation engages critical theory from transgender studies, concluding that since Matrona moves from one position of sexed or gendered intelligibility to another within her culture, she can be read as trans. After analyzing each of Matrona's transitions within the text, this dissertation then shows how the hagiographer centralizes gendered transitions within the text as a whole, presenting Matrona as a universal exemplar. The concluding chapter then offers preliminary thoughts for why a hagiographer may have written such a text in the mid-6th century, specifically the 540s CE. It then looks at the medieval reception history of the Life and other attestations to Matrona to confirm the dissertation's thesis and to speculate on the possibility of an historical Matrona.