My project intends to queer the history of masculinity and masculine dress in early modern history. There is evidence for a significant number of female sex workers wearing masculine attire in early modern Italy. However, there is yet to be a study that investigates the forms that this masculine expression took and women's motivations for gender nonconformity. My aim is to fill this gap in the scholarship, and to explore the following questions. Did sex workers choose masculine attire for only professional reasons (to attract homosexual male clients, as authorities worried), or as an expression of identity? By extension, is there a queer and/or trans history to be brought to light here? What can sartorial expression tell us about the permeability of gender boundaries in early modern, pre-Enlightenment Europe? I intend to use a combination of syphilis hospital records, court records, popular pamphlets and travel writing as source material. Syphilis hospitals recorded detailed notes on patients' attire. Since sex workers were particularly afflicted, an exploration of syphilis hospital records from across Italy could provide insight into how common it was for female sex workers to wear masculine attire, what kinds of garments were worn, and their materiality. Court record accounts will be useful for uncovering sex workers' motivations for cross-dressing. Travel writing, popular pamphlets and publications will provide evidence of sartorial expression embedded in urban space.