This paper examines the analytical viability of the concept of hegemonic masculinity in the historical studies of men and masculinities in modern Iran. I intend to argue that Connell’s concept of hegemonic masculinity despite its explanatory value may not be able to fully capture the complexity of material and social realities that determined the terms of the debate around masculinity in early-twentieth-century Iran. In the scholarship on Iranian masculinities, hegemonic masculinity is often reducible to the ideas and practices of a group of Western-educated elite, who utilized the Western standards of manliness exclusively to distinguish themselves from the masses. Such assertions are premised upon the assumption that there was a homogeneity of lifestyle and opinion among a diverse group of Iranian elites and therefore it could lead us to the wrong conclusion that these men can be clearly delineated from their rather traditional compatriots. I intend to show that a sharp delineation between a small group of Iranian elites and the rest of the populace does not reflect the fluidity of persons and ideas scattered along the axes of modernism and traditionalism. Moreover, informed by Tani E. Barlow’s analysis of conditions of “colonial modernity” in semi-colonial contexts, I argue for deconstruction of the Iranian/Western binary, seeking to open up new discussions of plurality versus shared patterns in both categories. While engaging with recent theoretical debates in the field of masculinity studies, I argue that to achieve a deeper historicisation of masculinities in Iran, instead of focusing on abstract discourses that are responsible for rise and demise of a hegemonic mode of masculinity, one should pay attention to the interpretive labor that individual men as particular knowers undertook to negotiate the hegemonic norms of their time. This shift in focus, I believe, allows historians to explore more adequately the complexity with which mechanisms of change and continuity operate within and outside the bounds of existing periodization.