Unlike common footwear, high heels have a role which makes standing position look as beautiful as possible for ladies. Compared with common walking shoes, it has been said that high heels has disadvantages in the performances. Here, the performances indicate sole stability, cushioning, smooth guidance and so on. The establishment of the high heel designing system pleases many ladies for performance as well as standing position. In this study walking motion analyses with high heels and some walking shoes with different sole structures are carried out. Judging from these analytical results, some quantitative parameters related difficulty in walking with high heels is identified. In order to improve the parameters, the relationship influences of heel plug shape and position on walking motion are quantitatively investigated. Therefore, it was confirmed that the heel plug shape and geometry were important designing parameters.