Flexible capacitive pressure sensors have attracted extensive attention due to their dynamic response and good sensing capability for static and small pressures. Using microstructural dielectric layers is an effective method for improving performance. However, the current state of microstructure design is primarily focused on basic shapes and is largely limited by simulation results; there is still a great deal of potential for further innovation and improvement. This paper innovatively proposes to increase the ladder structure based on the basic microstructures, for example, the long micro-ridge ladder, the cuboid ladder, and cylindrical ladder microstructures. By comparing 9 kinds of microstructures including ladder structure through finite element simulation, it is found that the sensor with a cylindrical ladder microstructure dielectric layer has the highest sensitivity. The dielectric layers with various microstructures are obtained by 3D printed molds, and the sensor with cylindrical ladder microstructure dielectric layer has the sensitivity of 0.12 kPa−1, which is about 3.9 times higher than that without microstructure. The flexible pressure sensor developed by us boasts sensitivity-optimized and operational stability, making it an ideal solution for monitoring rainfall frequency in real time.