The most significant medical function of graduated compression stocking (GCS) is to provide controlled support and pressure to the skin surface and the underlying tissues of the lower extremity, to prevent and treat venous disease, thus improving the blood circulation. However, due to lack of suitable technologies for the experimental measurements, the transfer mechanisms of the external pressure applied by GCS and internal stress states within the leg soft tissue were not well examined, which bring some difficulties to GCS compression design. The present study numerically simulated and analyzed surface pressure applied by GCS and the cross-sectional deformations at the target region of leg. The underlying tissues stress profiles as well as their dynamic alterations with time processing were presented and quantitatively investigated. Moreover, the medical significance of the cross-sectional inner stress distributions was discussed. The validation results indicated that the simulated pressure profiles applied by GCS agreed reasonably well with the measured ones. The developed biomechanical model can be used for prediction and analysis of the pressure functional performances applied by GCSs, thus helping us more understanding mechanisms of compression action and improving their medical functions.