Capturing human motions using wearable electronics provides tremendous opportunities for human–machine interfaces. However, current flexible sensors are always challenged due to the contradiction between the self-healing property and mechanical performance of the flexible matrix. Moreover, the strain sensing range of current sensors is always limited within 5% due to the ineffectiveness of conductive components upon larger strain. Inspired by the synergistic combination of hydrogen bondings and metal coordination, a self-healable elastomer was synthesized, which displayed a tensile strength of 1.73 MPa and a self-healing efficiency of 93%. Moreover, the designed flexible sensor using a synthesized silicone elastomer substrate and a carbon nanotube conductive component displayed a high gauge factor of 1198 contributed by the cooperation of the wrinkle structure and the microcrack mechanism. The flexible sensors exhibited a fast response of 129 ms due to the excellent adhesion of the conductive layer upon the substrate. Furthermore, a wearable intelligent gesture capturing system integrating an elastomer-based sensor and a wireless electronic control module was successfully developed to realize the real-time monitoring of hand gestures. Thus, the developed silicone elastomer-based sensor holds high potential for human–machine interfaces and provides a novel pathway for hand rehabilitation training.