Fitting is one of the most important functions for footwear designing, regardless of user's skill and category. The purpose of this study is the proposition of a new fitting evaluation method under the wearing condition. By using the sheet with highly sensitive sensors, pressure distribution between the foot and footwear was directly measured under the wearing condition. Then, we proposed PDI (Pressure Dispersion Index), which was calculated from differenciation of the pressure and the human sensitivity distribution. By comparison of PDI and sensual test, the validity of PDI was checked. Furthermore, the influence of foot type, shoe-size and local pressure upon the PDI was quantitatively discussed.