Pressure sensing is an important function of electronic skin devices. The development of pressure sensors that can mimic and surpass the subtle pressure sensing properties of natural skin requires the rational design of materials and devices. Here we present an ultra-sensitive resistive pressure sensor based on an elastic, microstructured conducting polymer thin film. The elastic microstructured film is prepared from a polypyrrole hydrogel using a multiphase reaction that produced a hollow-sphere microstructure that endows polypyrrole with structure-derived elasticity and a low effective elastic modulus. The contact area between the microstructured thin film and the electrodes increases with the application of pressure, enabling the device to detect low pressures with ultra-high sensitivity. Our pressure sensor based on an elastic microstructured thin film enables the detection of pressures of less than 1Pa and exhibits a short response time, good reproducibility, excellent cycling stability and temperature-stable sensing.