A brace worn by a user has side shell portions disposed in or on the lateral and medial sides portions of the brace to support the medial and lateral sides of the user's ankle. The shell may include a connecting center portion that extends under the foot of the user and couples the medial and lateral side shell portions. In certain embodiments, the connecting portion includes a plurality of flexible fingers oriented substantially towards the user's toes for yielding to the movement of the user's foot while maintaining the stability and orientation of the lateral and medial supports with respect to the user's ankle.