Clothing comfort includes complex combinations of several variables, such as fiber, yarn, fabric, garment design and fit, the way of wearing clothing layers, human factors and environment. Hence, some controversies over the dryness of microclimate are often resulted, especially in a multiple layered clothing system. A question still remains to be answered on the dryness of the microclimate next to skin in double layer or multi-layer clothing systems which incorporate hydrophilic and hydrophobic fibers. The purposes of this study are; firstly, to find out the change in the microclimate of single, double and triple layer clothing system step by step. Secondly, to investigate the effect of the arrangement of fabric layers with large differences in the moisture regain(cotton vs. nylon) on the microclimate, temperature and humidity gradient across the fabric layers. Finally, to elucidate the changes in the mode of dynamic heat and moisture transfer at each layer when a different third layer is placed on the double layer system. It was found that up to the second layer, dryness of innermost microclimate could be maintained when cotton faced the skin(C/N). However, when more permeable and hydrophobic third layers. (UWF) covers the double layer, the microclimate of C/N is no longer. drier than N/C. When nylon is exposed to the skin, a larger drop in vapor pressure across the first two layers occurred for model test. The innermost microclimate was not necessarily kept dry when the outermost layer dissipated more moisture due to the inefficient distribution of moisture.