The invention relates to an article of footwear having a hollow heel cavity that is adapted to receive a heel insert. A user can interchange heel inserts of varying thicknesses based on their activity, and is not required to change their footwear when undertaking a new activity. For example, hiking on a dirt trail may require a heel insert with less cushioning and more support, while running on pavement may require a heel insert with more cushioning and less support. The user can simply carry with him multiple heel inserts and replace the heel insert as needed to achieve a desired level of support, cushioning and comfort.