In this study, a stable and durable hexadecyltrimethoxysilane (HDTMS)/thermoplastic polyurethane (TPU) superhydrophobic film is successfully prepared by a simple and low-cost two-step method, namely, carrying out biomimetically hierarchical structures and low surface energy material modification concurrently. Meanwhile, effective parameters affecting the water contact angle (WCA) are studied and optimized. More importantly, under optimum parameters, the maximum WCA is 165°, the minimum slide angle (SA) is 3°, and the adhesion force is 13 μN, showing good self-cleaning performance. Besides, considerable mechanical stability to withstand 4000 tension or 5000 compression cycles, breathability, and moisture penetrability, as well as chemical resistance with sustained superhydrophobic properties in various harsh environments, are presented.