The intensive development of micro-/nanotechnologies offers a new route to construct sophisticated architectures of emerging soft electronics. Among the many classes of stretchable materials, micro-/nanostructured poly(dimethylsiloxane) (PDMS) has emerged as a vital building block based on its merits of flexibility, stretchability, simple processing, and, more importantly, high degrees of freedom of incorporation with other functional materials, including metals and semiconductors. The artificially designed geometries play important roles in achieving the desired mechanical and electrical performances of devices and thus show great potential for applications in the fields of stretchable displays, sensors and actuators as well as in health-monitoring device platforms. Meanwhile, novel lithographic methods to produce stretchable platforms with superb reliability have recently attracted research interest. The aim of this review is to comprehensively summarize the progress regarding micro-/nanostructured PDMS and their promising soft electronic applications. This review is concluded with a brief outlook and further research directions.