The quality and controllability of the building façade can significantly contribute to building indoor environmental quality (IEQ) as well as the building’s energy efficiency. Advanced technologies that support a façade’s dynamic response to climatic changes, such as electrochromic (dynamic) glazing, have emerged as smart systems for IEQ and environmental sustainability. This research summarizes a four-season study of office workers moving from a floor with conventional blinds to work environments equipped with smart dynamic glazing which changes tint in response to weather condition to control daylighting levels. Multiple occupant environmental satisfaction surveys were conducted over one year to investigate differences in environmental and psychological responses to office settings with manual, and often static, facades as compared to offices with dynamic glazing. This research confirms that dynamic glazing significantly affected occupants’ environmental satisfaction—enhancing individuals’ environmental perceptions and psychological health—as compared to manual blinds. It reveals that the occupants in work environments with dynamic glazing reported 21.7% higher productivity gains, 24.8% increased ability to relax, 12.7% improved concentration, 25.3% better moods and 29.4% greater alertness than when they were in offices in the same building with manual shading devices. Also, the dynamic feature of the smart glazing showed a significant contribution to perceived work productivity while enhancing positive emotional responses by an average of 26%.