Understanding past and current trends is crucial in the fashion industry to forecast future market demands. This study quantifies and reports the characteristics of the trendy walking styles of fashion models during real-world runway performances using three cutting-edge technologies: (a) publicly available video resources, (b) human pose detection technology, and (c) multivariate human-movement analysis techniques. The skeletal coordinates of the whole body during one gait cycle, extracted from publicly available video resources of 69 fashion models, underwent principal component analysis to reduce the dimensionality of the data. Then, hierarchical cluster analysis was used to classify the data. The results revealed that (1) the gaits of the fashion models analyzed in this study could be classified into five clusters, (2) there were significant differences in the median years in which the shows were held between the clusters, and (3) reconstructed stick-figure animations representing the walking styles of each cluster indicate that an exaggerated leg-crossing gait has become less common over recent years. Accordingly, we concluded that the level of leg crossing while walking is one of the major changes in trendy walking styles, from the past to the present, directed by the world’s leading brands.