Materials such as polyurethanes, silicones, and keratin may all fall under soft or similar materials in the bulk, but their compositions and surface energies differ vastly. These vast differences in surface energy and patterning potentially create great obstacles for engineering composite wearable devices. On the contrary, in biological systems, the multifunctional surfaces of animal and plant skins are uniquely evolved for fitness in their environments. Firstly, we enhanced stretchable optical mechanosensor durability and transmission length in poly(ester)urethane core sensors cladded with silicone as compared to previous mechanosensors using uncladded core fibers. I successfully doubled the adhesive strength between the poly(ester)urethane core and two-part platinum-cured silicone cladding via grafting TEOS-based silane coupling agents to the core surface without compromising (and often enhancing) sensitivity in multiple deformation modes. Secondly, we present the first engineering investigation of the Puff adder (Bitis arietans) snakeskin, the first known chemically cryptic land vertebrate. Thirdly, I present use of a quasi-hydrualic fluid that harnesses the friction of silica microsphere surfaces to create jamming assistive silicone actuators.