Enhanced dry adhesion of micropatterned polymeric surfaces has been frequently demonstrated. Among the design parameters, the cap geometry plays an important role to improve their performance. In this work, we combined experiments on single polyurethane mushroom-shaped fibrils (with stalk diameter 80 µm and height 125 µm) against flat glass, with numerical simulations implementing a cohesive zone. We found that the geometry of the mushroom cap strongly affects the interfacial crack behavior and the pull-off stress. The experimental and numerical results suggest that optimal adhesion was accompanied by the appearance of both edge and interior interfacial cracks during separation. Finite elemental analyses revealed the evolution of the interfacial stress distributions as a function of the cap thickness and confirmed the distinct detachment mechanisms. Furthermore, the effect of the stalk diameter and the Young's modulus on the adhesive force was established, resulting in an optimal design for mushroom-shaped fibrils.