The urban retail environment actively reflects changes in society today, as we exist in an undeniably interconnected world. Such movements have produced a geographically uneven market through which charity retailing has evolved. Charity retailers have become ubiquitous in their presence on the British high street – it is more surprising to discover urban areas without these retailers. Society has created the need for such retailers, but since their expansion in post World War Two Britain they have undergone a significant transformation – both economically and spatially. Charity retailers have become professional, profit maximising businesses as they developed from a stigmatised second-hand retailer relegated to undesirable retail locations have now emerged as fashionable signifiers of gentrification. This research considers the growth of charity retailers from an economic and spatial perspective, adopting the city of Edinburgh as its case study. Charity retailing is situated within the urban economy of the early twenty-first century, as a niche, which has evolved concomitant to the restructuring of the retail market. The paper addresses the lacuna of research in the third sector relative to charity retailers and is informed by socio-economic data and ethnographic studies. The research seeks to answer the question: How have charity retailers become so indelible in the British high street and how can they be understood?