To date, studies of outdoor thermal comfort (OTC) have focused primarily on physical factors, tending to overlook the relevance of individual adaptation to microclimate parameters through psychological and physiological behaviors. These adaptations can significantly affect the use of urban and outdoor spaces. The study presented here investigated these issues, with a view to aiding sustainable urban development. Measurements of OTC were taken at a university campus and in urban spaces. Simultaneously, a large-scale survey of thermal adaptability was conducted. Two groups were selected for investigation in a cold-winter-and-hot-summer (CWHS) region; respondents came from humid subtropical (Cfa) and hot desert (BWh) climates, according to the Köppen Climate Classification (KCC). Results showed that: (1) neutral physiological equivalent temperature (NPET) and preferred PET for people from the Cfa (PCfa) and BWh (PBWh) groups could be obtained with KCC; (2) PCfa adaptability behaviors were, subjectively, more adjustable than PBWh; (3) Clothing affected neutral temperature (NT), where NT reduced by approximately 0.5 °C when clothing insulation rose 0.1 Clo; and (4) Gender barely affected thermal acceptance vote (TAV) or thermal comfort vote (TCV) and there was a substantial relationship between thermal sensation, NT, and PET. These findings suggest ‘feels like’ temperature and comfort may be adjusted via relationships between microclimate parameters.