This paper reports the successful fabrication of flexible replicas with polymeric nanopillars using a process that combines nanosphere lithography, dry deep etching, soft-lithography, nanomolding and hydrophobic modification. The polymeric nanopillars with various sizes and three different periodicities have been implemented for systematic investigations on the interfacial properties on those surfaces. Such a flexible polymeric surface exhibited the maximum static contact angle of 166.8° at the nanopillars with a diameter of 60 nm, height of 710 nm and periodicity of 300 nm. The optimum aspect ratio should be less than 7 to avoid defects and collapses among those polymeric nanopillars during nanomolding. Metastable contact at the transition state indeed occurred on the parts of the intrinsic nanopillars, the experimental results of which also matched well to the classical theory of critical contact angle. Using hydrophobic modifications, metastable contacts among those polymeric nanopillars have further been eliminated. The polymeric nanopillars reported here were verified as having very strong adhesion as well as superhydrophobicity because such nanopillars made microdroplets hang firmly on the vertical surfaces of those designed replicas.