It has been determined that the silhouette of a flared skirt is influenced by the mechanical properties of the fabric and the number of gore panels used in the skirt. In order to study the factors influencing the comfort and aesthetic appearance of flared skirts, we used visual and wearing sensory tests to investigate the evaluation value of flared skirts made of several kinds of fabrics with different mechanical properties and having different numbers of gore panels. The results of factor analysis with the evaluation values obtained by the sensory tests revealed two factors about the impression formation of flared skirts. These were the effects of fabric bending and shear stiffness on the silhouette formation of skirts, and on the beauty of the form of the skirt. In the visual tests, the dynamic evaluation values were lower than the static evaluation values when the flared skirts were evaluated as being too difficult to slip between fabric and body (legs). This means that the fabrics with high coefficients of surface friction and high frictional resistance between fibers are evaluated as having “poor drapability” in dynamic tests. The evaluation value of “good for flared skirts” can be estimated using compound mechanical parameters of the bending stiffness, the shear stiffness, and thickness of fabrics obtained from both anisotropic seamed and seamless fabrics.