Green roofs and green and living walls are increasingly seen in cities, because they are an important strategy that addresses some key urban environmental issues and allows the achievement of different benefits. Among these, the most relevant ones are reduction of the “Urban Heat Island” effect, of rainfall contributions to the sewer system, of environmental impact and energy saving, and retention of harmful substance. The study aims to analyze different systems of greenery systems integrated (GSI), green roofs (GR), and green and living walls (GW-LW), as a possible retrofit technique of the envelope of heritage buildings and especially their applications in the context of historic cities in Italy, pointing out positive and negative aspects. Particularly, it pays attention to the green retrofitting of buildings and to the technical problems related to the installation of systems, since at the moment there are already several studies that show the environmental and microclimatic benefits of the integration of vegetation in architecture. This study tries to highlight the series of design procedures necessary both in the preliminary phase and then in the executive phase to relate the GSI to the existing building envelopes. The GR, from the results of the simulations conducted, demonstrate a greater simplicity in their construction, with improvements also from the point of view of the working loads on the existing structures, since the interventions are performed more easily than those on the facade. The study highlights the architectural needs that are not always considered such as the increase in the thickness of the roof and the related need to raise its edges, changing the perspective of the building. On the other hand, the GW and the LW show some complexity in their construction because they must deal with facades often rich in decorative elements and where openings affect the assemblage and connection works such as the tinsmiths of the intrados of the openings. It must be taken into consideration the necessity of having to drill masonry, often inhomogeneous, to connect fixings and the problems of stability this entails must be carefully analyzed.