The article approaches belonging using the conceptual tool of urban imaginary to demonstrate how a certain place can be represented in different ways, offering different scenarios for the emergence, explanation, and experience of belonging. Urban politics in St. Petersburg and Russia, in general, generate controversial imaginaries of the city and attach different meanings to belonging, forcing street artists to strike a balance between the hegemonic structures of governance and capitalism, local (national) and global (western), rebellion, and dependency, notably, to fulfill their ideas of belonging. Using sticker artists in St. Petersburg, based on ethnographic data, the article shows how young people assimilate several urban imaginaries and, following the logic inherent in each of these, position themselves and their activity in the city. Sticker artists are described as urban agents, who, by participating in place-making and transforming urban space using stickers, find their subjectivity and opportunities to wield microscale power.