Technology is continually undergoing a constituent development caused by the appearance of billions new interconnected “things” and their entrenchment in our daily lives. One of the underlying versatile technologies, namely wearables, is able to capture rich contextual information produced by such devices and use it to deliver a legitimately personalized experience. The main aim of this paper is to shed light on the history of wearable devices and provide a state-of-the-art review on the wearable market. Moreover, the paper provides an extensive and diverse classification of wearables, based on various factors, a discussion on wireless communication technologies, architectures, data processing aspects, and market status, as well as a variety of other actual information on wearable technology. Finally, the survey highlights the critical challenges and existing/future solutions.