The perceived differences between comfortable and uncomfortable shoes and the fit preferences in the different regions of ladies' shoes were explored. Twenty Hong Kong Chinese females participated in the study. Each participant wore and rated the different aspects of their own comfortable and uncomfortable shoes. The Wilcoxon signed rank tests showed significant differences in ten perceived characteristics between the comfortable and uncomfortable shoes. Among the ten were tactile, auditory and olfactory sensations. The ten items reliably (Cronbach alpha>0.9) distinguished between comfortable and uncomfortable shoes. There were no significant differences between comfortable and uncomfortable shoes for aesthetic-related characteristics. Further analysis on the fit ratings showed a significant impact on the fit preferences in the Toe region (p<0.0001), Metatarsophalangeal (MPJ) region (p<0.0001), Arch region (p=0.002) and Ingress/egress opening (p<0.001). Knowing the preferred type of fit can help establish a specification for comfortable shoes and also brings out the criteria that a comfortable shoe does not necessarily have the same perceived fit in every region of a shoe.