Plantar heel pain is a commonly encountered orthopedic problem and is most often caused by plantar fasciitis. In recent years, different shapes of insole have been used to treat plantar fasciitis. However, little research has been focused on the junction stress between the plantar fascia and the calcaneus when wearing different shapes of insole. Therefore, this study aimed to employ a finite element (FE) method to investigate the relationship between different shapes of insole and the junction stress, and accordingly design an optimal insole to lower fascia stress. A detailed 3D foot FE model was created using ANSYS 9.0 software. The FE model calculation was compared to the Pedar device measurements to validate the FE model. After the FE model validation, this study conducted parametric analysis of six different insoles and used optimization analysis to determine the optimal insole which minimized the junction stress between plantar fascia and calcaneus. This FE analysis found that the plantar fascia stress and peak pressure when using the optimal insole were lower by 14% and 38.9%, respectively, than those when using the flat insole. In addition, the stress variation in plantar fascia was associated with the different shapes of insole.