Nature-inspired fabrication of micro-structured superhydrophobic plastic film was aimed in this work in order to achieve smart materials with self-cleaning properties. Replicas of silicon masters were fabricated from different mixtures of base elements and by different processes. Corresponding microstructures were investigated by contact angle measurements, scanning electron microscopy and spectrophotometric analysis. Independently of the technology employed, the obtained films exhibited high contact angle value (larger than 150°), but while the acrylic polymers presented strong demoulding drawbacks, the polydimethylsiloxane (PDMS) films had good properties in terms of both contact angle and optical transparency. The results showed that most of the patterns realized by replica moulding and hot-embossing (on PDMS and polypropylene (PP), respectively) produced superhydrophobic self-cleaning surfaces.