This thesis looks to explore the aesthetic politics of the Robin Hood Gardens (RHG) estate in East London and its recent regeneration, problematising the debates that have emerged around its demolition and perceived ugliness/beauty. It challenges both the political revival of strategies that seek to blame supposedly 'ugly' architectural forms for wider social problems, as well as the narratives of those who seek to sanitise urban spaces through 'heritage-washing'. Instead, it advocates a position that reasserts the function of the estate as a site of home, and the social and material complexity that surrounds it. In order to do so it utilises a system of methods derived from both archaeological and geographic disciplines, as it pieces together the material, textual, artistic, and more-than-representational processes behind how the estate has become a symbol for discussions around gentrification within the city. Specifically, it engages with how 'images' of the estate have been produced and reproduced; including artwork of numerous 'RHG artists'; the audiovisual materials produced by the estate's developers (Blackwall Reach); as well as interviews with key heritage stakeholders and tenants of the estate, in order to present a discussion around how symbolic and representational practices continue to shape the material realities of the site. As a result, it concludes by challenging the various aesthetic and audio-visual strategies that promote forms of gentrification, instead advocating for perspectives which consider the estate in all of its intricacy.