Footwear comprising a sole for supporting a foot and an upper attached to the sole for covering the foot and adjoining ankle. The sole and upper define an interior of the footwear and is sized and shaped for receiving the foot and ankle. The upper has an outer shell that forms an exterior of the footwear and an inner lining that is adjacent the foot and ankle when they are received in the interior of the footwear. A compressible generally U-shaped pad is positioned between the shell and the lining of the upper. The pad has a bottom section and a pair spaced-apart side sections extending up from the bottom section. The pad is sized and positioned in the upper such that when the foot and ankle are received in the footwear, the bottom section of the pad is disposed immediately below a medial malleolus of the foot and the side sections of the pad extend up along opposite sides of the medial malleolus up to at least about the distal neck of the tibia. Upon movement of the foot and ankle in the footwear, the pad is adapted to apply an intermittent pressing force to tissue of the ankle below and on opposite sides of the medial malleolus to reduce swelling of the ankle. A U-shaped pad for the opposite (lateral) side of the ankle may also be provided.