Wearable technology to augment traditional approaches are increasingly being added to the arsenals of treatment providers. Wearable technology generally refers to electronic systems, devices, or sensors that are usually worn on or are in close proximity to the human body. Wearables may be stand-alone or integrated into materials that are worn on the body. What sets medical wearables apart from other systems is their ability to collect, store, and relay information regarding an individual’s current body status to other devices operating on compatible networks in naturalistic settings. The last decade has witnessed a steady increase in the use of wearables specific to the orofacial region. Applications range from supplementing diagnosis, tracking treatment progress, monitoring patient compliance, and better understanding the jaw’s functional and parafunctional activities. Orofacial wearable devices may be unimodal or incorporate multiple sensing modalities. The objective data collected continuously, in real time, in naturalistic settings using these orofacial wearables provide opportunities to formulate accurate and personalized treatment strategies. In the not-too-distant future, it is anticipated that information about an individual’s current oral health status may provide patient-centric personalized care to prevent, diagnose, and treat oral diseases, with wearables playing a key role. In this review, we examine the progress achieved, summarize applications of orthodontic relevance and examine the future potential of orofacial wearables.