An article of footwear is disclosed that incorporates an upper and a sole structure secured to the upper. The sole structure includes a midsole and an outsole. The midsole defines an aperture with a first sidewall, and the midsole includes an insert positioned within the aperture. The insert has a second sidewall, with at least a portion of the second sidewall being spaced from the first sidewall to define a space between the first sidewall and the second sidewall. The outsole is secured to the midsole, and the outsole defines a ridge that is positioned within a lower portion of the space and between the first sidewall and the second sidewall.