The capability to fabricate micro-nanostructured surfaces having superhydrophobic properties is of great importance in both scientific and industrial fields. Many superhydrophobic materials possess irregular or non-ordered surface roughness where the distribution of surface structures is random. However, the presence of ordered surface structures provides with myriad opportunities for studying the wettability properties via different phenomena. These studies highly depend on the roughness-property relationship including Cassie to Wenzel transition, water evaporation, droplet freezing, dynamic droplet impact, etc. Moreover, surface structures with different length scale have attracted many attentions recently in terms of durability against mechanical forces. Such surfaces can be produced via the combination of methods that produce various structure dimensions. In the present work, silicone rubber samples having ordered surface structures were fabricated via a micro compression molding system. We aimed to compare microstructured surfaces with 3-level micro-micro-nanostructured surfaces in terms of wettability characterization and superhydrophobic properties. Two templates were used to create surface structures. One was perforated sheets fabricated by laser milling to create micropillar as the first hierarchy (microstructures). The other was the chemically etched templates to create the second and third hierarchies (micro-nanostructures). The measured water contact angles were compared with the calculated equilibrium contact angles according to the thermodynamic analysis. A consistency was observed between the measured and calculated results.