Here, we examine the extension of smart retailing from the indoor confines of stores, outward to high streets. We explore how several technologies at the union of retail intelligence and smart city monitoring could coalesce into retail high streets that are both smart and sentient. We examine the new vantages that smart and sentient retail high streets provide on the customer journey, and how they could transform retailers’ sway over customer experience with new reach to the public spaces around shops. In doing so, we pursue a three-way consideration of these issues, examining the technology that underpins smart retailing, new advances in artificial intelligence and machine learning that beget a level of street-side sentience, and opportunities for retailers to map the knowledge that those technologies provide to individual customer journeys in outdoor settings. Our exploration of these issues takes form as a review of the literature and the introduction of our own research to prototype smart and sentient retail systems for high streets. The topic of enhancing retailers’ acuity on high streets has significant currency, as many high street stores have recently been struggling to sustain custom. However, the production and application of smart and sentient technologies at hyper-local resolution of the streetscape conjures some sobering considerations about shoppers’ and pedestrians’ rights to privacy in public.