Fitting comfort is one of the most important factors for runners in choosing suitable shoes. However, it is not always true that runners choose the best shoes from anatomical point of view, because fitting comfort is affected significantly by the preference and the habituation. For example, a runner with wide feet tends to prefer a tight shoe. This suggests that the true fitting comfort may not be realized by conventional research methods in which fitting comfort is evaluated by sensory evaluation. In this paper, we discussed a possibility of an objective assessment of the fitting comfort. Tight and loose fitting shoes were selected for a subject based on the morphology, and the mechanical interactions between the foot and shoe when worn by him were measured. As physical measurements representing the mechanical interactions, the skin temperature was measured using by a thermistor-thermometer at 3 locations of the foot during the treadmill running, and the relative displacement between the foot and shoe was measured at 2 locations of the foot using a high-speed camera. Using these physical measurements, the risk caused by the morphological misfit was examined. The results suggested risks of the blood flow disturbance and loss of power transmission, and a possibility to estimated the objective fitting comfort.