The aim of this study is to find out comfortable combinations of layered system for outdoor activities through water vapor permeability. Layering fabrics is an effective way of controlling water transport properties in fabric systems for outdoor activities and analysis of these systems may be useful for designing comfortable clothing. Seven fabrics were chosen for the experiments: two fabrics for base layer, two for the middle layer and three for the shell layer. A total of 12 different layered systems, which are all possible combinations were established using selected fabrics. The water vapor permeability was measured using JIS L1099 under isothermal and non-isothermal conditions. It was found that layered system was working together as a whole having influence on each layer, though every layer offers varying degree of water vapor permeability. Furthermore, it was also found that an optimal combination of the three layered system does exist although the combination may differ according to the ways. The shell layer is the greatest effect of water vapor permeability under isothermal and non-isothermal conditions within layered system.