In most of the contemporary urban spaces built in recent decades in Italy little attention is evident on the creation of environmental niches that are able to mitigate the microclimate. The following research aims to verify how the physical design of the outer space affects either the immaterial dimension of the space itself (livability, comfort), and the environmental performances of the surrounding buildings. The research supports the definition of the energetic-environmental requalification techniques to be used in the recovery phase of buildings. The analysis of the microclimatic features in the outdoor urban spaces, together with the implications in terms of comfort for those people who use them, opens new possibilities for the development of urban areas for what concerns both the new design and the requalification of the existing built-up area. Because of the complexity in terms of space-time variability of such parameters and of the wide set of activities in which people are committed, there have been so far very few attempts to understand the external comfort conditions, but mainly of how the external climatic effects could have an impact on the internal comfort conditions of the inhabited area.