Political discourses, public discussions, and studies in different fields have increasingly focused on the vulnerabilities affecting cities and on the possible responses to them, which are often traced back to urban resilience and sustainability. Research and debates in the field of retailing and consumption geographies are no exception. To carry out a critical analysis on the retail policies associated with the urban commercial change of the Naples city center, the case study is placed in the context of the literature review focusing on three concepts: spatial vulnerability, adaptive resilience, and territorialized sustainability. The analysis is conducted combining data, policy, and planning documents with long-term field research. The changing relationship between consumption practices, retail dynamics, and policies highlights a sort of hybridization of commercial and consumption central cityscapes, which is produced by the coexistence between retail-led phenomena of regeneration and forms of local resistance. The results of the research highlight, from a Mediterranean perspective, new general insights on the impact of selective forms of vulnerability and on the adaptive resilience strategies adopted, but most of all on the indispensable rethinking of the urban retail governance for the enhancement of urban livability, social cohesion, and locally sustainable lifestyles, activities, and places.