In Mumbai, informal dwellings such as slums and tenement housing, or chawls, are an outcome of the exponential increase in the city’s population after the upsurge of mills and industries during 19th-century British rule in India. Due to insufficient housing for the migrant working population, slums and pavement dwelling conditions came up at the doorsteps of factories, mills, and workshops within the city in the 1940s. By looking at the two distinct time periods, Colonial (1858-1947) and Post-Colonial India (1947- present), this paper intends to compare the living and housing condition of the so-called slum neighborhoods to the chawls of the city. Slums and chawls create unique living and resting scenarios that blur public and private spaces and are understood as informal and flexible, yet extremely functional living possibilities. This paper depicts how chawl settlements, as established and influenced by British colonialism, gave rise to slum settlements and public sleeping, and inspired different living scenarios in formal, informal, and pavement-dwelling conditions in post-colonial Mumbai. Further, the paper investigates how the chawl, through the administration of the state, has not only restructured the overall urban fabric but has also given way to non-conventional ways of living in both formal and informal settlements.