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's sidewall.