In this chapter I explore District One and District Six, two inner-city areas in Cape Town, South Africa, by means of a series of images gathered from its ruins. As a point of departure I quote Neville Lister. Lister is the first-person narrator of Ivan Vladislavić’s novel Double Negative (2011). He is a white middle-class young man from Johannesburg whose life overlaps with the city’s post-apartheid transformation. Vladislavić’s story, in which Lister becomes a photographer, was inspired by a volume of photographs of Johannesburg taken by renowned South African photographer David Goldblatt (Goldblatt 2010). As his protagonist finds himself in the post-apartheid city, Vladislavić highlights the complexities of attempts at representing a coherent visual narrative regarding South Africa’s disjunctive urban history. Over the course of the last decade or so I have visited Cape Town many times. My personal life converged with the city’s transformation as a result of fortuitous encounters I had first as a student, then as a tourist, and finally as a researcher. The six photographs discussed as part of this chapter are the product of collaborations in 2013 and 2014. Recalling the epigraph of Bettina Malcomess and Dorothee Kreutzfeldt’s book about Johannesburg, Not No Place (2013), I suggest the impressions conveyed by the images include, at best, ‘fragments of spaces and times’ representing post-apartheid Cape Town. Referring to Walter Benjamin and Thomas More, Malcomess and Kreutzfeldt describe the capture of the ‘double negative’ of the utopia (translated as ‘no place’), the materialization of ‘impossibility and always deferred potential’ (Malcomess and Kreutzfeldt 2013: 12). Like these critics, I focus on the difficulty of capturing the complex transformation undergone by Cape Town’s District One and District Six (see also Penrose, Chapter 8, for issues in capturing complex, capitalist transitions). Cape Town appeared as number one on the New York Times list ‘52 places to go to in 2014’. Journalist Sarah Khan wrote, ‘Cape Town is reinventing itself, and the world is invited to its renaissance’ (Khan 2014). It is a story about boutique shops, property values, gentrification, self-stylization, and the self-conscious craft of hipster appeal.