ABSTRACT
This chapter examines what are perhaps the most extensive disquisitions on this subject, namely a letter by Ambrose of Milan. There in, Ambrose adopts and adapts the tropes central to late ancient discourses to address 'why the Deuteronomic Law was so severe in pronouncing unclean those persons who wear garments of the other sex, whether men or women'. In the process, Ambrose re-scripts Roman manliness so as to place Christianity squarely at the center of both individual practice and imperial order. Thus throws into sharp relief the discourses surrounding dress, Empire, and masculinity in the precarious decades preceding the fall of the Western Roman Empire. Ambrose's concern rests primarily with male attempts at cross-dressing. Scholarship on the cross-dressing female saint in late antiquity has proliferated considerably in recent years. The latter has derived inspiration from scholarship on the woman martyr who in the process of her profession and death masculinizes herself.
