This paper investigates modes of gendered embodiment in pre-modern Arabic texts through episodes of cross-dressing. These are defined as episodes in which a character previously identified with masculine nouns and pronouns is presented with feminine nouns and pronouns, or vice versa, and in which some description of clothing acts as the means by which the switch in gender is perceived and/or explained. While these episodes have often been associated with the topos of disguise, I argue that they are not necessarily meant to be understood as moments of misrecognition, even when characters express surprise or astonishment upon having their gender perception challenged or undone. Drawing from insights in the fields of gender, sexuality, and trans studies, as well as recent scholarship on the pre-modern history of the body, this paper presents evidence from fifteenth- to seventeenth-century manuscripts of Alf layla wa-layla (1001 Nights), and related exemplars of what has been called Middle Arabic Literature, to suggest that bodies were seen as inseparable from social contexts in which clothing acted as a powerful signifier. This reading challenges assumptions that the sexed morphology of the body was understood to exist independently from contextualized modes of gendered embodiment, such that it would need to be hidden or disguised for a character to cross successfully from one gender to another. More broadly, it proposes an understanding of embodiment that exceeds the limits of the body as "enfleshed entity," to use Rajyashree Pandey’s words, and explores possibilities for new translations of Middle Arabic texts that resist defaulting to binary conceptualizations of bodies and clothing, sex and gender (Pandey 2016, 13). In doing so, this paper makes a contribution to recent efforts in the field of Islamic and Middle Eastern history to historicize the body by bringing literary evidence into a conversation so far dominated by legal, medical, and religious texts. It also contributes to the fields of gender, sexuality, and trans studies by examining gendered embodiment in a non-Western and pre-modern context.