This is the first example of processable, semi-fluorinated perfluorocyclobutyl (PFCB) aryl either polymers covalently bound to pendant polyhedral oligomeric silsesquioxanes (POSS) cages. The composites are prepared using a simple strategy, and demonstrate an increase in hydrophobicity (water-repelling) similar to that of commercial Teflon. The hydrophobicity is caused by the surface migration of the nanometer-sized POSS aggregates. This produces nanoroughness, with surface features mimicking those of the lotus leaf.