The purpose of this research is to find a distinctive but rather qualitative relationship between the thermal cognition acquired through daily experience in the built environment during summer and the indoor thermal conditions. We investigated the relationship between subjective responses and environmental quantities obtained from two experimental small wooden buildings: one has a radiative cooling system on the ceiling and the other has a convective cooling system. The ceiling surface temperature of the radiative cooling was set up to be much higher than the conventional radiative cooling panels in order to find a critical level of thermal condition. We sorted out 35 subjects into two types of lifestyles, namely, those exposed much to convective cooling and those using natural ventilation for long hours. We also sorted out the same subjects into two types, namely, those prefering to convective cooling and those who dislike convective cooling. The percentage of comfort votes tend to decrease as the indoor radiant temperature or air temperature increases, but there is quite a clear difference between those preferring to convective cooling and those who dislike convective cooling. It suggests that there exists such a thermal cognition built up through daily experience in the built environment, which is different from a group of people to the other, depending on what kind of cooling they are exposed to.