Retailers’ sustainability, although being an extremely topical issue, does not seem to have been fully examined yet, neither as regards its conceptualization, nor with reference to the dynamics which distinguish its sustainable actions. Despite the extreme heterogeneity of the definitions and interpretations related to the concept of sustainability, this dimension does not seem sufficiently investigated in the supply chain. In this regard, retailers are acquiring a critical position in the value chain, as actors in charge of transferring material flows and also concepts and values related to the offer. For these reasons, a sustainable dimension is no longer a possible option but becomes an inescapable perspective for these operators, an active stand in the supply chain in terms of capability to orientate sustainable development policies. In literature several are the approaches to the analysis of the sustainability issue: determinants, motivations, operation methods, implications on the company’s image and on purchase behaviours. However, few are the contributions which aim at investigating this issue from a management perspective, with particular reference to retail companies. Considering such aspects, this paper aims at understanding the meaning of sustainability according to retail operators and how it affects business actions, focusing both on the influence of sustainability on the adopted business formula and on the supply chain dimension. On a methodological level, exploratory research was carried out in a sample of retailers, completed by three case studies concerning three leading retailing companies.