Electronics are evolving from “brittle” to “flexible” and are expected to advance to “stretchable.” Development of stretchable semiconductor materials is a key step for the realization of highly deformable transistors. This article introduces the technological strategies for achieving stretchable polymer semiconductors, including a geometrical approach, formation of a nanofibril network, microcrack formation, and synthesis of new polymers. We conclude with perspectives on further development of stretchable polymer semiconductors.