Informality, associated with street vendors, is now seen as a generalised mode of metropolitan urbanisation. Street vendors form an important part of several economies around the world and are seen as a vital source of livelihood and employment opportunity for the low-skilled, lower-income class of the population. A closer understanding of profiles of street vendors and the nature of complexities present in the business of street vending—studied through the supply chain processes of product procurement and distribution—helps one in observing an entwined relationship between what are perceived as “informal” or “formal” in the urban ecosystem. This study on street vendors working across Kolkata emphasises the need to adopt an inclusive view to urban “informal” arrangements, providing a comprehensive picture in identified local market spaces. Our research focuses on two critical aspects: (a) capturing samples of oral account(s) from merchants/vendors operating in local markets across Kolkata, and (b) gauging the supply-chain (inventory) process of products procured and sold by street vendors in these markets. The observations made from the field help highlight the complexities present in studying urban supply-chain processes—especially street vending businesses—that form the core of most urban metropolises in cities (such as Kolkata) and are representative of the Global South.