Emerging scientific consensus reveals that spending time outdoors promotes wellness. However, several forces impede time spent outdoors, such as opportunity, safety, and adverse weather. While uncomfortable weather intuitively decreases time outdoors, acclimatization research suggests a counterintuitive process: outdoor exposure enhances physiological adaption to adverse weather, thereby increasing perceived comfort in subsequent outings and even during a single outing in some situations, which, in turn, increases time outdoors. Therefore, this study preliminarily investigated whether time spent outdoors is associated with perceptions of weather and ambient temperature, apart from actual weather. This study attempted to isolate the role of self-reported weather-and thermo-comfort in predicting time spent outdoors by controlling for motivational and social factors. Residing in the same locale, participants were exposed to identical weather conditions. To enhance recall accuracy, participants daily reported time spent outdoors and weather- and thermo-comfort across a 7-day period, producing 175 time-comfort entries. Cox regression analyses show that greater perceived comfort with weather and greater perceived comfort with the temperature are associated with significantly more time spent outdoors, adjusting for motivational and social factors. Results also show that participants who wanted to go outdoors, compared to those who had to go outdoors, reported significantly greater weather comfort. Physiological and other relevant research findings on the human relationship with weather contextualize the study’s rationale and results.