The fragility of the micro-nano structure makes superhydrophobic coatings highly susceptible to stress, resulting in a decrease in their superhydrophobic and anti-icing performance. In this work, we proposed a new insight to improve durability by incorporating a thin layer of self-healable elastomer with a dynamic network on the micro-nano structure. We constructed superhydrophobic coatings (EP/SiO₂/BFVSE) with a three-layered structure of the epoxy resin/silica nanoparticle/silicon elastomer. The silicon elastomer (BFVES) with a B–O dynamic cross-linked network and fluorinated moieties was synthesized by graft polymerization on vinyl silicon oil. The preparation route is facile and convenient for mass production. BFVES has rapid self-healing properties for scratches at room-temperature, underwater and at −18 °C. EP/SiO₂/BFVSE preserved apparently higher CAs after being immersed in pH = 1, pH = 13, and NaCl solutions for 96 h as compared with the EP/SiO₂ coating. In a water striking environment, the CA of EP/SiO₂/BFVSE was slightly decreased to 153°. SEM images further reveal that the recovery of superhydrophobicity and icephobicity is attributed to the self-healing behavior of the boroxine-containing silicon elastomer. The EP/SiO₂/BFVSE coating also possesses additional self-healing ability under chemical oxidation. The high durability of the self-healable superhydrophobic coating enables great application potential in aircraft, marine vessels, and outdoor facilities in harsh environments.