Stiff thin films on soft substrates are both ancient and commonplace in nature; for instance, animal skin comprises a stiff epidermis attached to a soft dermis. Although more recent and rare, artificial skins are increasingly used in a broad range of applications, including flexible electronics, tunable diffraction gratings, force spectroscopy in cells, modern metrology methods, and other devices. Here we show that model elastomeric artificial skins wrinkle in a hierarchical pattern consisting of self-similar buckles extending over five orders of magnitude in length scale, ranging from a few nanometres to a few millimetres. We provide a mechanism for the formation of this hierarchical wrinkling pattern, and quantify our experimental findings with both computations and a simple scaling theory. This allows us to harness the substrates for applications. In particular, we show how to use the multigeneration-wrinkled substrate for separating particles based on their size, while simultaneously forming linear chains of monodisperse particles.