Generative methods have evolved over the previous decade to become reliable for hardware design. Given their characteristics, these methods have found notable use in designing wearable assistive devices (WADs) such as orthoses, prostheses, and exoskeletons. Challenges in designing such devices may be characterized as lightweighting, actuator load reduction, adjustability, and responsiveness. In this work, we look at the strategies employed by these methods and their features—and generalize a framework for the design of assistive wearables. An overview of the evolution of the design of WADs is included, along with an exploration of the advent of generative design, to contextualize the two together. Works concerning generative methods to design wearable assistive hardware are examined for their objectives, design methods, and generative strategies. Presented thereafter is a selection philosophy—tabled as a mapping of strategy alternatives and methods to objectives. The same has been exemplified in the context of a case—a short-term injury necessitating the use of an ankle–foot orthotic (AFO) device.