The poor performance of clear glazing usually makes conventional windows accountable for substantial heat exchanges and glare problems that lead to both thermal and visual discomfort, particularly in highly glazed façades. Static solar control films have been installed in the last years as a retrofitting solution of existing windows with the potential to reduce excessive solar gains, however, studies that assess their performance are still scarce in the literature. In addition, the development of dynamic film technologies, such as photochromic films that can autonomously and reversibly react (chromatic change) to the presence of solar radiation and reduce the solar transmittance of the glazing system, has been instigated. The aim of this study was to evaluate the annual percentage of working hours with thermal and visual comfort in an office room with a double clear glazing retrofitted with solar control films (a static reflective film and a dynamic photochromic film), considering three European climates, through a calibrated simulation model constructed in EnergyPlus. The photochromic film was more effective on promoting useful illuminance levels (83–88%), while the reflective film was associated to lower perceptible glare levels (2–6%). When considering a free-float regime, the reflective film made it possible to achieve higher percentages of working hours within thermal comfort conditions (19–42%), compared with the photochromic film (3–19%). With the air-conditioning system operating, the photochromic film was more effective on promoting thermal comfort (47–93%), against the reflective film (30–66%), but the potential climatization energy needs associated with its performance act as a drawback.