The postwar Allied occupation of Istanbul from 1918 to 1923 brought international geopolitics into the intimate sphere of daily life for all residents of the city. Every person, whether refugee, cosmopolite, foreign worker, longtime resident or rural migrant, felt the constraints of postwar poverty, and the landscapes of the city’s various districts were variously imbued with powerful mixtures of hope and/or anxiety regarding the city’s future stability and sovereignty. Although much has been written about gender tensions in early twentieth century Istanbul, particularly regarding the historic cultural politics surrounding women’s bodies in a modernizing society that retained an ideal mother role for women, the relationships between urban geopolitics and formations of gender in the occupied city remain an understudied topic. This paper integrates the themes of Turkishness, wealth, urban memory, territoriality, and religion to show their convergence in the problem of masculinity during the occupation. I mine memoirs, satirical essays, and caricatures written in Istanbul during the occupation by male Turks for depictions of urban masculinity and gendered political anxiety. For example, many male stereotypes in satirical essays and caricatures were failures: the wealthy but unsophisticated boor, the poor loser, the cuckold, the drunkard, and the ignorant hoja. Memoirs illuminate male grief for the Ottoman Turkish city and helplessness in the face of Allied power exerted on the streets of the city and at the desks of the Paris Peace Conference. This research demonstrates how the urban experience of occupation influenced cultures of gender for Istanbulite Turkish men.