To investigate the influence of the heat transfer of the air layer in the micro gap between skin and clothing in heat transfer while wearing clothing, sealed and unsealed air layers of various widths (≦10.0 mm)with a woolen cloth inserted, were placed into the vertical heat transfer measuring unit, attached to the heat transfer measuring device. The sealed and the unsealed air layers were undergoing heat transfer due to the flow (fluctuation) of air. There was heat transfer to the exterior space due to the flow of air in the unsealed air layer. The sealed air layer had higher heat retention than the unsealed air layer. In the sealed air gap, the total heat transfer coefficient of the air layer with the cloth inserted was smaller than that of the air layer without the cloth inserted, and the heat retention was high. In the unsealed air layer also, inserting a cloth improved heat retention.