The virtual try-on technologies of the current level have limitations with material expression as well as some difficulties with commercialization. There are differences in simulation results and subjective evaluations perceived by consumers according to the types and physical characteristics of materials used in virtual try-on simulations. This study were to analyze the exterior clothing shapes and visual images from 3D virtual try-on simulations with materials whose drapability was differentiated and then test the accuracy of the expression of the drapability of the materials. The study carried out 3D virtual try-on simulations by selecting flared skirts as an item to best express differences in drapability along with five materials of different physical properties and offered some basic data for greater utilization of virtual try-on simulations by comparing and analyzing them with the exterior shapes and visual images of actual flared skirts. The analysis results of hemline shapes between actual and virtual try-on according to the types of materials showed no match among the quantitative items of exterior shapes factors. There were no significant differences in the visual images except for "soft" according to the simulation methods, which means that the items can serve as part of a scale for visual image comparison. It is necessary to reflect quantitative numbers regarding "drapability" proposed in the study simulation software and to continue to build a systematic database for virtual simulations by investigating and testing various materials.