Slippery liquid-infused porous surfaces (SLIPSs) are biomimetic, ultra-smooth surfaces characterized by low friction and self-cleaning properties, which are attained by impregnating lubricants into porous microstructures. Nevertheless, conventional SLIPS faces the issue of lubricant depletion when exposed to static inclined orientations and dynamic environmental stresses, thereby limiting their durability in applications such as anti-fogging and anti-frosting. In this study, we introduce slippery liquid-infused doubly reentrant surfaces (SLIDRSs), which integrate doubly reentrant microstructures with a functional nanocoating to enhance lubricant retention. These hierarchical structures substantially increase the pinning force, effectively trapping lubricants even under extreme conditions. When compared to conventional micro-pillar-based SLIPS, SLIDRS demonstrates an average 17 % improvement in lubricant retention across static tilt angles ranging from 0° to 90° and a 37 % enhancement under dynamic rainfall erosion conditions (0.3 in./h), ensuring robust performance in diverse environments. Rotational testing indicates a mere 20 % lubricant loss at 1000 rpm. SLIDRS exhibits durable passive anti-fogging, anti-frosting, and self-cleaning capabilities, along with excellent chemical stability. Furthermore, their integration with liquid metal electrodes (LMEs) facilitates active heating while preserving optical transparency and conformal adaptability to curved surfaces, thereby expanding the potential for deicing and anti-icing applications in aerospace systems, automotive windshields, and telecommunication equipment.