Mechanic interaction between foot and sock is an important factor affecting wearing comfort. In this paper, we introduced a finite element (FE) approach to model the contact between the foot and sock. A biomechanical foot model consisting of bones and soft tissues and an orthotropic and elastic sock model were constructed for simulating the contact process. By using the model, we simulated the process of wearing a sock, which consisted of two kinds of materials. The stress and pressure distributions in the sock as well as that in the foot were predicted. The comparison between the pressure measurements at several geometrically characteristic points and the predicted pressures confirmed that the model was able to simulate the sock wearing condition and predict the pressure exerted by socks. It was also demonstrated that the skin pressure depended on the curvature of the contact surface and the stress in the fabric. The developed FE model allows us to carry out parametric analysis on socks of different styles and materials with a relatively quick and easy way and to provide guidance to the functional design of socks.