Abstract In this paper we examine the energy demands required for building heating and cooling over a real urban area and how these relate to urban microclimatic parameters; as a result we furthermore show how urban planning can benefit from such relevant considerations for the benefit and prospect of energetically sustainable societies and cities. Specifically, we conduct a multiscale analysis on a validated dataset of the urban energy demands of the Westminster Borough building stock over different seasons as well as on relevant urban information data obtained for the same borough. The aim of this analysis is to investigate the link between urban form characteristics (such as the emerging urban dynamic parameter of the city breathability along with the building height and building packing density) – with the associated urban energy demands for heating and cooling. By using a rigorous scale-adaptive approach, we unveil the intensity of this link between urban energy demands and the urban features and we furthermore deduce how sensitive such links are to the size of the district considered. This new knowledge enables end-users to decipher the degree of impact of proposed actions attributed to technical insights, based on the size of the region over which a decided action is to be implemented in the context of an energy management policy.