The integration of flexible electronics with optics can help realize a powerful tool that facilitates the creation of a smart society wherein internal evaluations can be easily performed nondestructively from the surface of various objects that is used or encountered in daily lives. Here, organic‐material‐based stretchable optical sensors and imagers that possess both bending capability and rubber‐like elasticity are reviewed. The latest trends in nondestructive evaluation equipment that enable simple on‐site evaluations of health conditions and abnormalities are discussed without subjecting the targeted living bodies and various objects to mechanical stress. Real‐time performance under real‐life conditions is becoming increasingly important for creating smart societies interwoven with optical technologies. In particular, the terahertz (THz)‐wave region offers a substance‐ and state‐specific fingerprint spectrum that enables instantaneous analyses. However, to make THz sensors accessible, the following issues must be addressed: broadband and high‐sensitivity at room temperature, stretchability to follow the surface movements of targets, and digital transformation compatibility. The materials, electronics packaging, and remote imaging systems used to overcome these issues are discussed in detail. Ultimately, stretchable optical sensors and imagers with highly sensitive and broadband THz sensors can facilitate the multifaceted on‐site evaluation of solids, liquids, and gases.