Wearables as medical technologies are becoming an integral part of personal analytics, measuring physical status, recording physiological parameters, or informing schedule for medication. These continuously evolving technology platforms do not only promise to help people pursue a healthier life style, but also provide continuous medical data for actively tracking metabolic status, diagnosis, and treatment. Advances in the miniaturization of flexible electronics, electrochemical biosensors, microfluidics, and artificial intelligence algorithms have led to wearable devices that can generate real-time medical data within the Internet of things. These flexible devices can be configured to make conformal contact with epidermal, ocular, intracochlear, and dental interfaces to collect biochemical or electrophysiological signals. This article discusses consumer trends in wearable electronics, commercial and emerging devices, and fabrication methods. It also reviews real-time monitoring of vital signs using biosensors, stimuli-responsive materials for drug delivery, and closed-loop theranostic systems. It covers future challenges in augmented, virtual, and mixed reality, communication modes, energy management, displays, conformity, and data safety. The development of patient-oriented wearable technologies and their incorporation in randomized clinical trials will facilitate the design of safe and effective approaches.