Animals are evolved to acquire rich tactile sensations that allow them to adapt to and survive the changing environments. Robots built with conventional hardware, on the other hand, have yet to achieve the same level of sophistication for generally useful applications. In this dissertation, I present my work on a new class of multifunctional stretchable sensors that, taking inspirations from biology, provide rich tactile sensations for soft robots through novel designs combining optical sensing principles and functional organic materials.In the first part, I present stretchable distributed fiber-optic sensors (DFOS) that can resolve multimodal deformations to mimic the enabling distributed multimodal sensing function in skin’s mechanoreception. With principles inspired by silica-based DFOS systems, stretchable DFOS exploits a combination of frustrated total internal reflection and wavelength-modulated absorption to distinguish and measure the locations, magnitudes, and modes (stretch, bend, or press) of mechanical deformations. We further demonstrate multilocation decoupling and multimodal deformation decoupling through a stretchable DFOS–integrated wireless glove that can reconfigure all types of finger joint movements and external presses simultaneously, with only a single sensor in real time. In the second part, I present autonomous self-healing and damage resilient stretchable optical sensors that enable soft robots to detect, adapt to, and survive damages via feedback control. Intrinsic self-healing materials can recover their mechanical properties post damages via dynamic bonds for infinite times autonomously or with external stimuli. Elasticity, toughness, and autonomous self-healing abilities are contradicting properties in self-healing elastomers to optimize simultaneously. Due to exacerbated viscoelasticity contributed by the dynamic bonds, self-healing stretchable electronic sensors suffer from drift, hysteresis and limited strain range. Combing optimization in material design and sensor design, a stretchable optical sensor has been achieved that autonomously self-heals in room temperature and provides dynamic measurements to 140% strain with no hysteresis or drift. Moreover, the sensor is damage resilient to substantial material removal by virtue of material toughness and optical sensing principle. A soft pneumatic quadruped with the self-healing sensors and self-sealing actuators is demonstrated to survive and adapt to sever damages.