<p>Re-entrant surface textures are promising for achieving high liquid repellency; however, their practical application is often limited by fabrication complexity and demolding difficulty. The purpose of this study is to propose a nanoimprint-based fabrication method for asymmetric re-entrant textures inspired by the skin structure of filefish, originally evolved for antifouling in aquatic environments, and to simultaneously achieve high static water repellency and excellent droplet mobility in air. In this approach, a symmetric mold fabricated by femtosecond-pulsed laser processing was employed, and asymmetric structures were generated through controlled, directional demolding during thermal imprinting of polymethylpentene films, enabling the formation of asymmetric structures without requiring asymmetric mold geometries. The effects of geometrical parameters, including pitch and convex width, on wettability were systematically investigated. The results revealed that decreasing the pitch significantly enhanced the apparent contact angle, while smaller convex widths further amplified this effect. Notably, the fabricated surfaces exhibited outstanding liquid-repellent performance in air, achieving both a maximum apparent contact angle of 161.5 ± 3.1° and a minimum sliding angle of 1.9 ± 2.3°. However, the process window, defined as the range of processing conditions that enables stable imprinting, became increasingly restricted with increasing structural scale due to enhanced adhesion and demolding resistance. These findings demonstrated a simple yet effective strategy for fabricating asymmetric re-entrant structures and provided design guidelines for scalable production of high-performance liquid-repellent surfaces.</p>