Dynamic thermal insulation systems (DTISs) can adapt to external environment conditions and help to reduce energy consumption and increase occupants’ thermal comfort, contributing towards the mitigation of overheating. DTISs adjust their configuration to optimize heat transfer through the façade. In this study, the performance of a DTIS was assessed through laboratory tests and numerical simulation. The DTIS is based on the ventilation of an air gap that facilitates the heat exchanges between the exterior and the interior. To extend the results of the experimental campaign, a set of scenarios was assessed based on numerical simulation. The results of the laboratory tests showed that the R-value obtained when the mechanical ventilation of the air gap is off (insulation state) is 3.89 m2.°C/W. In comparison, when it is on (conductive state), the R-value is 1.56 m2.°C/W, which corresponds to a reduction of approximately 60%. The results of the simulations showed that, when the shading system was on, the higher U-value was useful more than 50% of the time with discomfort, increasing to 75% when the shading system was off.