A wrinkled adhesive surface is prepared by swelling a laterally confined elastomer layer with a polymerizable monomer composition. Swelling the elastomer layer spontaneously produces a wrinkled surface, and the wrinkles are then stabilized by polymerizing the polymerizable monomer composition. The stabilized wrinkled surfaces prepare by the method can exhibit substantially enhanced adhesion relative to smooth surfaces of the same material. The stabilized wrinkled surfaces can also exhibit adhesion that is repeatable through many cycles of contact with and separation from another surface. The adhesive characteristics of the stabilized wrinkled surfaces can be tailored by manipulating the size of the wrinkles.