The analysis of interaction phenomena occurring between the plantar region of the foot and insole was investigated using a combined experimental–numerical approach. Experimental data on the plantar pressure for treadmill walking of a subject were obtained using the Pedar® system. The plantar pressure resultant was monitored during walking and adopted to define the loading conditions for a subsequent static numerical analysis. Geometrical configuration of the foot model is provided on the basis of biomedical images. Because the mechanical behaviour of adipose tissues and plantar fascia is the determinant factor in affecting the paths of the plantar pressure, specific attention was paid to define an appropriate constitutive model for these tissues. The numerical model included sole and insole, providing for friction contact conditions between foot–insole and insole–sole pairs as well. Two different numerical analyses were performed with regards to different loading conditions during the gait cycle. The plantar pressure peaks predicted by the numerical model for the two loading conditions are 0.16 and 0.12 MPa, and 0.09 and 0.12 MPa in the posterior and anterior regions of the foot, respectively. These values are in agreement with experimental evidence, showing the suitability of the model proposed.