A nanostructured surface may exhibit low adhesion or high adhesion depending upon fibrillar density, and it presents the possibility of realizing eco-friendly surface structures with desirable adhesion by mimicking the mechanics of fibrillar adhesive surfaces of biological systems. The current research uses a patterning technique to fabricate smart adhesion surfaces: one-, two- and three-level hierarchical synthetic adhesive structure surfaces with various fibrillar densities and diameters. The contact angles and contact angle hysteresis were measured to characterize the wettability. A conventional and a glass ball attached to an atomic force microscope (AFM) tip were used to obtain the adhesive forces via force–distance curves and to study the buckling behavior of a single fiber on the hierarchical structures.