Developments in digital and communication technology are now reaching the realms that border on science fiction. Computing devices are no longer items that we use in our homes and places of work and carry in our bags and pockets. We can now wear those devices. This article focuses on this development. In doing so, it explores old and recent developments in wearable technology with a focus on their current and potential use in the field of healthcare and medical education. It also highlights the challenges that are likely to face this technology. Moreover, it attempts to provide some insights into the prospects of this technology from the theoretical perspective of the theory of disruptive innovations as proposed by Clayton Christensen and his colleagues from Harvard Business School.