This article discusses the ways that Lefebvrian thinking on urbanization has found a purchase in Indian urban and anti-caste scholarship, and conversely, how compelling new figures of the urban have emerged from Indian scholarship that productively enliven Lefebvrian categories, refusing any separation between the experimentalism of everyday life and the political economy of space. The article explores a sense of “itinerant urbanization” at two levels: at an empirical level, it describes the urban as a tentative condition of becoming that is always on the move and inter-mixed with its non-urban other. At a more theoretical level, itinerant urbanization is an acknowledgment of the tremendous generativity of Indian scholarship’s own itineracy, which produces a transversal relation with not only metropolitan urban theory, but also agrarian Marxism and rich scholarship on embedded geographies of caste. The article suggests that theorizations of the Indian urban—some expressly drawing on Lefebvre, but many not—offer spatial figures that work with but extend Lefebvrian dynamics of concentration and extension. It specifically draws from anti-caste thought to discuss circles, fractals and segmented planes as ways to capture emergent productions of space that avoid center/periphery binaries and to add explicitly postcolonial and anti-caste political commitments to urbanization debates.