This article looks at the relatively recent tendency to aestheticize life in Nairobi’s working-class and informal neighbourhoods in different forms of art and media. It focuses on two case studies – Steve Bloom’s photobook, Trading Places: The Merchants of Nairobi (2009) and the first issue of the Kenyan literary magazine Kwani? (2003). These are compared to the collectively performed poem ‘Mistaken Identity’ (2019) by a group of poets from the neighbourhood of Kayole, to show that the street aesthetics in the two cases rest on distance, while the meaning-making in the poem rests on proximity. Distance in this context takes several forms, such as the gap between socio-economic classes and actual physical distance, but I register it on the level of epistemology. The poem also articulates a form of epistemological proximity between, first, the forms of meaning-making that can be seen in both the text and the visual and performative components of the video, and, second, the place that is portrayed. Rather than arguing that proximity is preferable to distance as a basis of meaning-making, this article attempts to theorize the emergence of a specific aesthetic. This aesthetic presents itself as an aesthetic because the particular forms of social stratification and concomitant social distance between communities and neighbourhood (which have emerged in Nairobi since 2000) allow an economic, political and cultural elite to re-discover the city, which they experience as simultaneously strange and familiar.