an aspect of the present invention includes a footwear assembly comprising : an upper and a sole assembly connected to the upper . the sole assembly has a footwear assembly comprising a sole assembly connected to an upper . the sole assembly has a midsole made of a first material and having a forefoot portion , an arch portion , a heel portion , and a sidewall extending around a lateral side , a medial side , and a heel side of the midsole . a stiffener is connected to the midsole . the stiffener is made of a second material stiffer than the first material . the stiffener has a base portion adjacent to the arch portion and at least one of the forefoot portion and the heel portion of the midsole . the stiffener has a side stabilizer and a heel wrap coupled to the base portion . the side stabilizer is adjacent to the sidewall in at least one of the arch portion and forefoot portion . the heel wrap is adjacent to the heel side and at least one of the lateral side and medial side of the midsole &# 39 ; s sidewall .