Foot strike mode and footwear features are known to affect ankle joint kinematics and loading patterns, but how those factors are related to the ankle dynamic properties is less clear. In our study, two distinct samples of experienced long-distance runners: habitual rearfoot strikers (n = 10) and habitual forefoot strikers (n = 10), were analysed while running at constant speed on an instrumented treadmill in three footwear conditions. The joint dynamic stiffness was analysed for three subphases of the moment–angle plot: early rising, late rising and descending. Habitual rearfoot strikers displayed a statistically (p < 0.05) higher ankle dynamic stiffness in all combinations of shoes and subphases, except in early stance in supportive shoes. In minimal-supportive shoes, both groups had the lowest dynamic stiffness values for early and late rising (initial contact through mid-stance), whilst the highest stiffness values were at late rising in minimal shoes for both rearfoot and forefoot strikers (0.21 ± 0.04, 0.24 ± 0.06 (Nm/kg/°∙100), respectively). In conclusion, habitual forefoot strikers may have access to a wider physiological range of the muscle torque and joint angle. This increased potential may allow forefoot strikers to adapt to different footwear by regulating ankle dynamic stiffness depending upon the motor task.