This work reported the dynamic effects of water droplet impact on flat, porous and pincushion structure films of star shaped polyhedral oligomeric silsesquioxane (POSS) fluorinated acrylates, POSS-poly(trifluoroethyl methacrylate)8 (POSS-(PTFEMA)8) and POSS-(poly(trifluoroethyl methacrylate)-b-poly(methyl methacrylate))8 (POSS-(PTFEMA-b-PMMA)8), using the breath figure method. The porous and pincushion structure films with different surface chemical compositions were obtained by controlling the copolymer structure and temperature and by stripping of the surface. The water contact angles on the different films were measured, and the water droplets on the pincushion structure films when reversed at 45°, 90°, 135° and 180° were also studied. It was found that the pincushion structure films revealed a water adhesion ability. Furthermore, the water droplet impact behavior on these films was investigated. The morphology variations of water droplets, spreading diameter of the droplets, energy conversion, restitution coefficient and adhesion force were examined. Finally, the schematic illustration of water droplets under the static and dynamic states in contact with the pincushion and porous structure surfaces was proposed. It is critical to materialize various applications such as microdroplet transportation, soil erosion, spray painting, anti-icing surface and antifouling agents for textiles.