The main objective of this study was to examine how contact pressure on the dorsal surface of the foot changes with varying shapes. Ten healthy young men (22.1 ± 0.6 years) with independent walking ability were recruited in this study. We measured the anthropometric characteristics of the foot. Shoe size for the experiment was individually decided based on the obtained anthropometric data. Subsequently, FlexiForce® sensors were attached to the dorsal side of the first metatarsophalangeal joint (P1), intermediate cuneiform (P2), and pternion (P3) to measure the contact pressure during walking. In addition, foot switch sensors were used to determine the gait cycle. At P2, some participants with a higher foot height showed a lower increase in contact pressure during the loading response or pre-swing phases than did participants with a lower foot height. The observed distribution of the contact pressure on the dorsal foot might be caused by the change in the shape of the shoes and the foot joint movement during walking.