Footwear including a sole for supporting a foot and an upper attached to the sole for covering the foot. The sole and upper define an interior of the footwear sized and shaped for receiving the foot. The upper has an inner surface adapted for engaging the foot when it is received in the interior of the footwear and an outer surface forming an exterior of the footwear. The upper also includes compressible cushioning permitting the upper to conform to the foot when it is received in the interior of the footwear to improve the fit of the footwear. The compressible cushioning is sized, shaped and positioned in the upper to at least partially surround a protrusion extending from the foot and is at least partially omitted from an area of the upper corresponding to the protrusion. Thus, a recess is formed in the upper for accommodating the protrusion to relieve pressure applied to the foot by the upper at the protrusion. The protrusions which are thus accommodated include protrusions at the heads of the first and fifth metatarsals, a portion of the fifth toe corresponding to the fifth proximal phalanx, and portions of the ankle corresponding to the distal heads of the tibia and fibula.