As digital platforms are woven into urban life, they become an intrinsic part of the urban experience. Here we examine how representations on digital platforms reflect and shape urban change. Which groups produce and share these representations? What places do they picture? What are their aesthetic registers and norms? And what are the material consequences of these representations? Elaborating on the concept of ‘discursive investing’ introduced by Zukin et al., we address these questions in a case study of Javastraat, a shopping street in a gentrifying neighbourhood in Amsterdam East. On the basis of an analysis of Instagram posts, street observations and interviews, we show that gentrifiers use social media to express their identity status, often creating posts that serve as advertisements for hip and high-class establishments. Meanwhile, other establishments are largely absent from digital platforms, with the notable exception of a number of shops that changed their aesthetics to appeal to gentrifiers. We further show that these uneven representations have material consequences, changing the aesthetics and composition of the shopping street.