Compression bandage (CB) as a porous material should provide both graduated pressure and thermal comfort properties to enable air permeability, heat transfer, and liquid perspiration out of the human body. The main factors affecting thermal comfort properties are the temperature difference between environment and skin, yarns’ structure and material, fabric thickness, porosity, areal density, number of fabric layers, trapped air, and fabric structure. Thermal resistance (Rct) and water vapor resistance (Ret) are evaluated for four types of woven CBs. All bandage types were applied at the range of extension (10–80%) using both two- and three-layer bandaging on thermal foot model (TFM). Rct values are compared with measured results by the Alambeta instrument, whereas Ret test is performed on the Permetest device. Thermal resistance is significantly decreased when increasing the bandage extension from 10 to 40%, then it is slightly increased by increasing the extension from 40 to 60%, after that it is decreased especially at 80% extension due to lower bandage thickness and higher compression.