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, and the midsole including: a first insert positioned within the first aperture, the first insert having a shape of at least three connected rounded regions that are arranged to extend through a heel region of the sole structure and into a midfoot region of the sole structure, 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 rounded regions being positioned closer to the lateral side than the medial side, and a center of a third of the rounded regions being positioned closer to the medial side than the lateral side, and a second insert 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, wherein the at least three connected rounded regions include at least three tangentially-connected circular regions. 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, and the midsole including: a first insert positioned within the first aperture, the first insert having a shape of at least three connected rounded regions that are arranged to extend through a heel region of the sole structure and into a midfoot region of the sole structure, 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 rounded regions being positioned closer to the lateral side than the medial side, and a center of a third of the rounded regions being positioned closer to the medial side than the lateral side, and a second insert 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 having a shape of at least three connected rounded regions that are arranged to extend through a heel region of the sole structure and into a midfoot region of the sole structure, 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 rounded regions being positioned closer to the lateral side than the medial side, and a center of a third of the rounded regions being positioned closer to the medial side than the lateral side, and a second insert 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, wherein the at least three connected rounded regions include at least three tangentially-connected circular regions.