The inherent ability of bio‐inspired underwater superoleophobicity to prevent oil/oily fouling underwater makes it appropriate for a wide range of applications related to environmental remediation, bio‐adhesion, microfluidics, chemical sensing, etc.; however, the co‐association of mechanical durability and optical transparency is essential for realistic performance. While the design of mechanically durable and absolutely optically transparent underwater superoleophobic coating remains challenging, here, a covalently cross‐linked and chemically reactive sol‐gel conversion process is introduced through 1,4‐conjugate addition reaction to achieve a substrate‐independent and tolerant coating for orthogonally modulating the underwater oil wettability, optical transparency, and even mechanical properties of highly deformable porous and fibrous substrates. The post‐modification of residual chemical reactivity in the prepared coating allows to embed underwater superoleophobicity, and the β‐amino‐ester‐cross‐links improve the mechanical property of selected deformable substrates. Moreover, it displayed unperturbed performance even after prolonged (30 days) exposures in practically relevant chemically harsh aquatic conditions—including extremes of pH, artificial seawater, surfactant contaminated water, etc. The approach is successfully applied to coat various substrates—including porous, fibrous, and planar objects, and it would be useful in protecting various relevant marine infrastructures from oil/oily fouling, and various other potential applications.