In this study, the mechanical properties and preferences of natural and artificial leathers were analyzed. The leathers were classified based on mechanical properties affecting their preferences. The mechanical properties of the leathers were measured via the KES-FB system, and an expert survey was conducted to evaluate leather preference. Leathers possess different mechanical properties depending on the manufacturing process and structural characteristics. Furthermore, differences were observed in the mechanical properties of natural and artificial leather. The mechanical properties of the leathers were related to the preferences for hand and bags. Accordingly, the leather was classified into three clusters. The leathers that were preferred for hand were not preferred for bags, and those preferred for bags were not preferred for hand. Therefore, different development strategies are needed, depending on the type of leather. Natural leather for bags should be light and have good compression elasticity along with its existing mechanical properties, whereas artificial leather should be light and have improved tensile resilience.