Since the beginning of the new millennium, a plethora of works has been published on the making of the ‘creative city’ and the urban impact of the creative economy. So far, however, limited recognition has been given to how the development of cultural industries and the creative economy as a whole influences urban transformation in the rapidly urbanising Global South, especially in Africa. In Cape Town, a steadily growing number of creative industries and ‘culturepreneurs’ are carving out new spaces from the city’s highly contested urban setting. Over the past five years, the mixed-use, inner-city fringe area of Woodstock has seen the incessant arrival of creatives from various sectors. Travelling alongside is a property sector geared towards catering specifically for the creative industries’ spatial demands by turning old industrial structures – the remains of Woodstock’s former capacity as national hub for clothing, food processing and other light manufacturing – into creative centres hosting international film studios, leading galleries and designer ‘theatre retail spaces’. After setting the stage through a comprehensive introduction to the rise of the creative economy in South Africa and Cape Town, this article tunes into the current local development of Woodstock, based on extensive field research in the area. It traces ways and forms of conflict but also new social interfaces between the new creative tenants and the old established community, on the one hand pointing to problematic issues like lingering gentrification, sociospatial polarisation and lopsided cultural representation while also trying to flesh out some of the opportunities for finding the right frequency of engagement between creative industries and spaces of vernacular creativity within Cape Town’s post-apartheid urban realm.