This chapter posits that retail supply chains need to rethink their activities in the light of current economic, social, environmental and ecological subjects/approaches to provide better sustainable leadership. Supply chain activities have dramatically changed over the last four decades, from production through consumption, and contributed to current developments and issues which have led to humankind being at a cusp in its relationship with the environment. Raising concerns across holistic and global supply chains, such as increasing pollution and waste and depletion of natural resources, suggest a step-change and new way of thinking are required about how we engage with the planet, including in retail supply chains. Three research-driven examples are used to illustrate the breadth and depth of such concerns. The first discusses how retailers may not be providing food access and security to all consumers through existing store networks and distribution. The second discusses retail segmentation not really understanding the needs of younger consumer generations who are becoming a larger market segment each passing year, and who may genuinely not be interested in embracing massive consumption patterns like previous generations. The third example explores the increase of e-commerce: online retailing is supplanting traditional in-store retailing across the globe, which is more costly, encourages poor operational and managerial practices in fulfilment and return centres, and negatively impacts retailer costs and the natural environment due to increased movements. Finally, suggestions are provided for retailers to strategically adapt to these issues to incorporate smart, responsible and accountable leadership so the retail sector develops sustainability leadership.