New medical compression technologies that are simultaneously low‐profile, facile to don, and dynamic—applying medical compression only when needed—can expand the use of wearable compression, increase patient compliance, and lead to better medical outcomes. Dynamic and conformal wearable compression devices are presented that can be donned in a low‐stiffness state and transition into a high‐stiffness and, consequently, high‐compression state, on‐demand. These devices are enabled by active textiles developed from custom NiTi filaments that remain inactive at room temperature and accomplish actuation proximal to the human body surface. Further, these compression devices exploit NiTi material hysteresis to sustain a high‐compression state post‐heating and upon equilibrium with the body surface temperature for thermally‐comfortable, on‐body performance. Two case study examples—1) a consumer medical compression device and 2) a custom astronaut compression device—demonstrate the generalizability and flexibility of the engineering and design methods to develop a range of dynamic, tunable, and conformal compression devices with different goals and requirements. Further, this work demonstrates a roadmap for developing wearable systems that can accommodate a range of users without sacrificing system performance. This research opens doors for new NiTi‐based medical and consumer applications that interface with the body surface.