Retailers choose location on the basis of accessibility measures and attractiveness of potential places. Firstly, this research focuses on understanding and measuring the morphological characteristics of typical urban locations in order to provide a critical interpretation of urban commercial patterns. Moreover, more than ever before, traditional urban retail systems are endangered. Online shopping, upsurges in competition, recession and market saturation are, among the causes of a slow but steady transformative process, leading to the closure of physical stores throughout the city. If the presence of empty spaces within the urban tissue is an issue by itself, the closure of retailers is even worse. Indeed, they play a vital role in the liveability of a city by contributing to the vitality and the attractiveness of the neighborhood. Furthermore, the closure of retailers negatively interferes with the economic sustainability of the city and, thus, with its viability. As an even bigger problem, ripple effects might emerge as a consequence. Indeed, the agglomeration of empty spaces in a suburb tend to move consumers, that are more likely to purchase in attractive places, elsewhere. This consumers’ reaction might speed up the closure of retailers that are still active in that neighborhood which has become more and more unpleasant. Hence, secondly, this research aims at understanding the dynamics that lead to the closure of commercial spaces within the urban realm. Among the others, on-line retailing and the above-mentioned ripple effect matter.