The phenomenon of ‘cultural crossdressing’ – western tourists marking their visit to Palestine, or the region more generally, with a studio portrait taken in ‘traditional costume’ – has been well addressed within Orientalist frameworks, though less attention has been focused on the significant Arab participation in the practice, particularly in the early decades of the twentieth century as the Ottoman Empire gave way to the British Mandate. This paper will investigate the deployment of ‘traditional’ costuming in photography as a marker of identity. It will question the cultural negotiation that the deployment of such costuming engenders, particularly with regards to notions of class, urban-rural divides, gender, nationalism and belonging. It will argue that ‘traditional’ costume was central to the deployment and production of a putative authenticity. It will consider the ways in which this notional authenticity was a cultural articulation of nationalism that impacted on identity formation processes during the formative rise of Arab nationalism. In addressing the relationship of nationalism to cultural cross dressing, it will contrast the transgressive nature of the practice in articulating differing articulations nationalist identity in the Palestinian urban and middle-classes as well as other communities. By analysing photographic evidence of the adoption of cultural crossdressing by local communities, this paper ultimately asks what the transgressions of class, gender and urban-rural divides can tell us about how urban communities articulated new modes of nationalism and how they related to their compatriots.