Flexible pressure sensors are a key component of electronic skin (e-skin) for use in future applications ranging from human healthcare monitoring to robotic skins and environmental risk detection. Here, we demonstrated the development of a highly sensitive, simple, and low-cost capacitive pressure sensor, which acted as a flexible capacitive dielectric, based on a microstructured elastomeric template that could be fabricated over a large area. To achieve this goal, the dielectric template was prepared simply by stretching and releasing a flexible Ecoflex film to produce wrinkled surface microstructures with a feature size on the order of tens of micrometers. The effects of the wrinkled surface microstructure on the sensing performance were systematically investigated by comparing the nonwrinkled film, one-side wrinkled film, and double-side wrinkled film. The response and release times of the double-side wrinkled pressure sensor were improved by 42% and 25% in comparison with the values obtained from the unwrinkled case, respectively. These results showed that the introduction of wrinkled surface microstructures to the elastomeric template efficiently enhanced the pressure sensor performance. We also demonstrated that our sensor could be used to detect a variety of changes in the surroundings, such as variations in the angle of a stimulus, object loading/unloading, or an exhaled breath.