Background: Alterations in the lower limb kinematics and kinetics of diabetic patients have been reported in previous studies. Inappropriate choices of orthopedic insole materials, however, fail to prevent diabetic foot ulcers and modify abnormal gait. The aim of this study was to quantitatively compare the effects of contoured insoles with different materials on the kinematics of and kinetics changes in the diabetic elderly during gait. Methods: There were 21 diabetic patients who participated in this study. Three-dimensional (3D) experimental contoured insoles constructed of soft (i.e., Nora Lunalastik EVA and PORON® Medical 4708) and rigid (i.e., Nora Lunalight A fresh and Pe-Lite) materials with Langer Biomechanics longitudinal PPT® arch pads were adopted. An eight-camera motion capture system (VICON), two force plates, and an insole measurement system—Pedar® with 99 sensors—were utilized to obtain the kinematics and kinetics data. The plug-in lower body gait model landmarks were used for dynamic data acquisition during gait. The corresponding data from five gait cycles were selected and calculated. Results: The range of motions (ROMs) of the ankle joint (p = 0.001) and knee joint (p = 0.044) were significantly influenced when the contoured insoles were worn in comparison to the barefoot condition. The joint moments of the lower limbs with maximum ankle plantarflexion during the loading response and maximum knee and hip flexions were significantly influenced by the use of contoured insoles with different materials in the diabetic elderly. The peak plantar pressure (PPP) of the forefoot (p < 0.001), midfoot (p = 0.009), and rearfoot (p < 0.001) was significantly offloaded by the contoured insoles during the stance phase, whilst the PPP of the rearfoot (p < 0.001) was significantly offloaded during the swing phase. Conclusions: The contoured insoles, especially those constructed with soft materials, significantly offloaded the PPP during gait—hence accommodating certain abnormal gait patterns more effectively compared to going barefoot.