The primary objective of conservative care for the diabetic foot is to protect the foot from excessive pressures. Pressure reduction and redistribution may be achieved by designing and fabricating orthotic devices based on foot structure, tissue mechanics, and external loads on the diabetic foot. The purpose of this paper is to describe the process used for the development of patient-specific mathematical models of the second and third rays of the foot, their solution by the finite element method, and their sensitivity to model parameters and assumptions. We hypothesized that the least complex model to capture the pressure distribution in the region of the metatarsal heads would include the bony structure segmented as toe, metatarsal and support, with cartilage between the bones, plantar fascia and soft tissue. To check the hypothesis, several models were constructed with different levels of details. The process of numerical simulation is comprised of three constituent parts:​ model definition, numerical solution and prediction. In this paper the main considerations relating model selection and computation of approximate solutions by the finite element method are considered. The fit of forefoot plantar pressures estimated using the FEA models and those explicitly tested were good as evidenced by high Pearson correlations (r=0.70-0.98) and small bias and dispersion. We concluded that incorporating bone support, metatarsal and toes with linear material properties, tendon and fascia with linear material properties, soft tissue with nonlinear material properties, is sufficient for the determination of the pressure distribution in the metatarsal head region in the push-off position, both barefoot and with shoe and total contact insert. Patient-specific examples are presented.