Since footwear flexibility impacts functional design factors, numerous studies have investigated footwear bending stiffness. However, the various methods used to measure footwear bending stiffness have some limitations. Hence, the scope of this study was to develop and quantify the reliability of a novel test set-up for measuring footwear bending stiffness. A test set-up consisting of a hydraulic testing machine, a bending apparatus and a fixation unit was created that fulfilled the requirements specified in the initial phase of the study. The test set-up was evaluated by testing 15 different boots in three series of measurements. Bending stiffness of the boots ranged from 0.61 ± 0.03 Nm/° to 2.38 ± 0.08 Nm/°. Two-way analysis of variance test yielded that the test set-up enabled the reliable measurement of footwear bending stiffness. Relative measurement uncertainty ranged from 1.3 % to 6.1 %.