Green facades and roofs are prevalent in various building typologies across most climatic regions. In warm contexts with the presence of cooling needs, numerous empirical and theoretical studies showcase the effectiveness of these systems in regulating the internal thermal conditions of spaces. The research addresses a gap in the literature concerning experiences with living green roof and green wall systems in cold climatic conditions. Considering the climate in Quito, characterized as a 4C type climate according to ASHRAE, which entails combined heating and cooling needs, this research aims to assess and compare the thermal performance through an empirical methodology based on the construction of two physical prototypes—one with vegetated elements and one without. Throughout the investigation, a comprehensive database of temperature and relative humidity records was compiled from four experiments conducted during both dry and rainy seasons. The findings of the experimental study indicate that these systems not only help in lowering temperatures during the day but also possess the capability to maintain temperatures during the night and early morning and addresses that during periods of heavy rainfall, yet the vegetated prototype exhibited consistent thermal performance, indicating resilience to adverse weather conditions. These findings suggest that green walls and roofs can maintain their effectiveness even in challenging weather scenarios.