Virginia Woolf's famous proclamation, "as a woman, I have no country. As a woman I want no country. As a woman my country is the whole world," is now considered one of the defining moments in the formulation of modernist cosmopolitanism. Woolf's declaration of a world citizenship locates the crux of modernist cosmopolitanism in renouncing national loyalties and transcending cultural boundaries. However, transcending boundaries is not equivalent to dissolving national borders and imposing a widespread homogeneity on distinct communities. How does modernist cosmopolitanism preserve cultural difference without invoking binaries of superiority/inferiority? How does postcolonial literature alter the modernist legacy in the context of rising ethnocentric nationalism and insistence on preservation of cultural and ethnic 'purity'? My dissertation uses theories of cultural and political cosmopolitanisms, nation formation, and urban studies to address these questions. In particular, Plurabilities of the City examines how cosmopolitanism is especially manifest in urban cultures and how a variety of urban spatial practices reveal multiple forms of cosmopolitanism. Through a series of case studies, comprising British, Irish, and Bengali novels and ranging from James Joyce to Bernardine Evaristo, I study how literary expressions of metropolitan cosmopolitanism evolve over time. I examine the representations of Dublin, London, and Kolkata in both modernist and postcolonial novels from Ireland, Britain, and India (West Bengal). My project responds to Douglas Mao and Rebecca Walkowitz's call for a new modernist studies by exploring different iterations of modernism in Irish, British, and Bengali literatures. By focusing on various modes of cosmopolitanism my project distinguishes cosmopolitanism from transnationalism, multiculturalism, globality, and planetarity. It concludes that modernist and postcolonial literary representations of cosmopolitanism perform several functions. They are committed to transcending cultural borders, insistent on preserving cultural specificity in intercultural exchanges, and resistant to homogeneity. Overall, Plurabilities of the City dismantles the binary between the Global North and the Global South and showcases how global modernist studies and postcolonial studies are informed by each other.