An article of footwear incorporating an upper and a sole structure secured to the upper, the sole structure comprising: a midsole extending along at least a portion of a longitudinal length of the footwear and having a lateral side and a medial side, the midsole defining a first aperture and a separate second aperture (32b, 32c), and the midsole including: a first insert positioned within the first aperture, the first insert extending through a heel region of the sole structure and into a midfoot region of the sole structure, the first insert having a shape of five overlapping or tangentially connected circular regions, a center of a first of the rounded regions being substantially equidistant from the lateral side and the medial side, a center of a second of the circular regions being positioned closer to the medial side than the lateral side, a center of a third of the circular regions being positioned closer to the lateral side than the medial side, and a fourth and a fifth of the circular regions being positioned in the midfoot region of the sole structure and corresponding in location with an arch area of the foot, a second insert (40b, 40c) positioned within the second aperture, the second insert having a shape of at least two connected rounded regions that are positioned in a medial-to-lateral direction with respect to each other; and an outsole secured to the midsole. a midsole extending along at least a portion of a longitudinal length of the footwear and having a lateral side and a medial side, the midsole defining a first aperture and a separate second aperture (32b, 32c), and the midsole including: a first insert positioned within the first aperture, the first insert extending through a heel region of the sole structure and into a midfoot region of the sole structure, the first insert having a shape of five overlapping or tangentially connected circular regions, a center of a first of the rounded regions being substantially equidistant from the lateral side and the medial side, a center of a second of the circular regions being positioned closer to the medial side than the lateral side, a center of a third of the circular regions being positioned closer to the lateral side than the medial side, and a fourth and a fifth of the circular regions being positioned in the midfoot region of the sole structure and corresponding in location with an arch area of the foot, a second insert (40b, 40c) positioned within the second aperture, the second insert having a shape of at least two connected rounded regions that are positioned in a medial-to-lateral direction with respect to each other; and a first insert positioned within the first aperture, the first insert extending through a heel region of the sole structure and into a midfoot region of the sole structure, the first insert having a shape of five overlapping or tangentially connected circular regions, a center of a first of the rounded regions being substantially equidistant from the lateral side and the medial side, a center of a second of the circular regions being positioned closer to the medial side than the lateral side, a center of a third of the circular regions being positioned closer to the lateral side than the medial side, and a fourth and a fifth of the circular regions being positioned in the midfoot region of the sole structure and corresponding in location with an arch area of the foot, a second insert (40b, 40c) positioned within the second aperture, the second insert having a shape of at least two connected rounded regions that are positioned in a medial-to-lateral direction with respect to each other; and an outsole secured to the midsole.