Emerging in the early twentieth century, the “modern girl” was a global typecast with distinctive hairstyle, fashion, and attitude. This stereotypical image of the modern girl made an appearance in cities and the press across the Middle East and North Africa, but its emergence and depictions in twentieth century Iran has rarely been examined. While some in cultural milieus condoned her emergence as a symbol of modernity, others censured the modern girl and her representations for “imitating” the west and fostering decadence. By tracing the cinematic representations of this typecast in an urbanizing Iran, this paper explores the competing discourses that shaped modern womanhood in the first half of the twentieth century. In the early twentieth century, interactions and exchanges between a smorgasbord of ethnic, religious, and political communities shaped an urban cosmopolitan culture in cities, most notably in the city of Tehran. Newspapers, photography, cinema, gramophone, and radio, not only reified this heterogeneous culture, but also redefined it in a rapidly changing society. In this context, competing models of modern life emerged that worked to shape and reshape modern Iranian subjects. The urban modern girl, now becoming a more visible member of the society, was subjected to competing discourses that envisaged her place in the public sphere, as she negotiated her own identity in the city. Investigating the representations of this nascent category in film and print culture from the 1900s to 1950s, I demonstrate how the modern girl came to symbolize urban contestations, as she exemplified the city’s freedoms and limitations to reshape oneself and one’s future. By no means a homogeneous figure, the modern girl drew on the opportunities that cities such as Tehran presented to refashion herself into an urban figure with a unique sense of style.