Wearable electronic devices with multifunctions such as flexible, integrated, and self-powered play a crucial role in the fields of health monitoring, motion monitoring, and human-computer interaction. However, their core basic components, flexible pressure sensors, face challenges including poor long-term stability and insufficient real-time sensing accuracy. In order to solve the challenges of long-term, stable, and accurate sensing of the sensor, this paper prepares polydimethylsiloxane (SHPDMS) with intrinsic self-healing property and designs a high-sensitivity self-healing capacitive flexible pressure sensor with dual microstructures (grating microstructured electrodes and microporous dielectric layer) as the substrate based on SHPDMS. Specifically speaking, the self-healing of the sensor under mild conditions was realized by introducing reversible imine bonds with low bonding energy into the polydimethylsiloxane (PDMS) flexible substrate, which solved the problem of the material's long-term service durability. A grating-like microstructure was introduced into the flexible electrode by using a spotted bamboo taro leaf as a template, and a dual microstructure sensor was constructed by combining it with a microporous dielectric layer doped with single-walled carbon nanotubes. This way reduces the elastic modulus of the dielectric layer, improves the dielectric constant of the sensor under loading, and thus significantly improves the sensor's sensitivity and extends the measurement accuracy in a low-stress range. The prepared self-healing flexible sensor achieves a sensitivity of 3.6 kPa-1, a minimum detection limit of 5 Pa, a response recovery time of less than 80 ms, and stability over 5000 cycles, which exceeds most previously reported silicone rubber-based capacitive flexible sensors.