This paper attempts to analyze the urban dualities created by colonialism in a rather unusual setting: ?stanbul, which was never ‘officially’ colonized. Looking at the urban reform programs and transformation of the built environment in Galata and Pera at the late nineteenth- and early twentieth-century, I try to show how a strict historical and urban duality was constructed within the larger geography of ?stanbul. I further claim that only within such a historical conjecture one can attempt to explore the place of the Allied Occupation of 1919 in the city’s history. Such a perspective, I argue, may speak to the curious amnesia in the scholarship about the Occupation, as well as to the neglect of the struggles that shaped the district, its peoples and its built environment. The conventional historiography treats the transformation of Galata and Pera during the late nineteenth-century within a continuous narrative that ties the unique place the district had in the early years of the Ottoman rule to the later developments, reiterating the ‘non-Muslim’ and ‘European’ character which was supposedly unchanged in the previous four centuries. Rather than echoing this narrative, I look at Galata and Pera from a threefold perspective of modernity, colonialism, and capitalism; and I argue that the dichotomous positioning of the district against the Muslim, oriental, old, ‘historical peninsula’ was a late nineteenth-century imagination – a necessary discursive and spatial formation examples of which we see in other colonial cities. I also critically engage with the nostalgic accounts of the district that praise an associated multicultural environment, or even cosmopolitanism, by looking at the lower class non-Muslims and Muslims, who were not part of this ‘belle-époque’ European culture.