Surface functional materials have aroused extensive attention due to tremendous application foreground in the anti-icing technology. However, durability and longevity are still critical problems that restrict their practical applications. In this work, a sustainable water-repellent surface was facilely constructed through comb-like WPU of crystalline octadecyl pendant groups. Because of octadecyl crystals tilting on the surface, the comb-like WPU exhibit dynamic water-repellent properties, which are mainly related to laying-down phase of crystals. Meanwhile, the surface wetting behavior is reversible switching between the sliding state and the pinning state due to phase transition, and the surface self-replenishing occurs in this process. Besides, on the basis of excellent adhesion to several substrates, these comb-like WPU make the crystallization temperature of water decreased by 9 °C approximately, and the ice adhesion strength (τice) before and after 150 abrasion cycles maintain only 3 kPa at −20 °C, exhibiting remarkable and regenerable anti-icing and deicing properties. Importantly, the transformation from laying-down phase to standing-up phase of crystals generates the successive deicing effect of interfacial slippage and micro-cracks, resulting in low τice below 20 kPa after continuous 100 icing/deicing cycles. These findings provide a facile way to design a promising surface material for enhancing endurance of anti-icing coatings.