Viscoelastic inserts are commonly used as artificial shock absorbers to prevent neuropathic foot ulcerations by decreasing pressure on the sole of the foot. Unfortunately, there is little scientific information available to guide physicians in the selection of appropriate insole materials. Therefore, a novel methodology was developed to form a rational platform for biomechanical characterizations of insole material durability, which consisted of in vivo gait analysis and in vitro bioengineering measurements. Results show significant differences in the compressive stiffness of the tested insoles and the rate of change over time in both compressive stiffness and peak pressures measured. Good correlations were found between pressure-time integral and Young's modulus (r2 = 0.93), and total energy applied and Young's modulus (r2 = 0.87).