This article presents a pilot study of thermal comfort and adaptive behaviors of occupants who live in naturally ventilated dormitories at the campus of the National University of Singapore. A longitudinal survey and field measurement were conducted to measure thermal comfort, adaptive behaviors and indoor environment qualities. This study revealed that occupants living in naturally ventilated buildings in tropics were exposed to higher operative temperatures than what American Society of Heating, Refrigerating and Air-Conditioning Engineers (ASHRAE) comfort standards recommend for naturally conditioned spaces. However, they still felt that such conditions were acceptable. Two behavioral adjustments were found to have profound impacts on occupants’ acceptance of the imposed heat stresses: (1) increasing the indoor air velocity by turning on mechanical fans and opening the door/windows for cross ventilation, and (2) reducing clothing insulation by changing clothes and dressing in fewer clothes. Higher indoor air velocities were also associated with greater satisfaction with indoor air quality. The future study should develop a statistical model to correlate adaptive behaviors with temperature variations for tropical climates.