Durable functionalization on polypropylene (PP) surfaces is always a key problem to besolved. Coatings with low surface energy peel off easily especially under extreme conditions, owing to their weak adhesion. In this paper, side groups of both polyhedral oligomeric silsesquioxane (POSS) and alkane are grafted to polypentafluorophenyl methacrylate (PFP), and then PP blends with these side-group modified PFP are obtained through a melt-blending process. It is found that POSS can result in surface segregation and provide hydrophobicity in blends. Microfibers are formed because of the orientation effect during the tensile testing, which furtherly promotes mechanical strength. Significantly, alkaneside-groups can be entangled with PP segments, which brings about cross linking. Therefore, with crosslinking and synchronous orientation of POSS, the elongation at the break of blends is greatly increased up to 974%. The final blend demonstrates quite durable hydrophobicity under many extreme conditions, such as repeated tape peeling, ultrasonic washing, strong friction, and soaking in strong acid (pH = 1), strong alkali (pH = 14) and alcohol. The heat and UV resistance of the blend are also obviously improved. This study will develop anovel and facile strategy to endow PP with durable hydrophobicity as well as greatly enhanced mechanical properties.