Background Graduate medical education (GME) has emphasized the assessment of trainee competencies and milestones; however, sufficient in-person assessment is often constrained. Using mobile hands-free devices, such as Google Glass (GG) for telemedicine, allows for remote supervision, education, and assessment of residents. Objective We reviewed available literature on the use of GG in GME in the clinical learning environment, its use for resident supervision and education, and its clinical utility and technical limitations. Methods We conducted a systematic review in accordance with 2009 PRISMA guidelines. Applicable studies were identified through a review of PubMed, MEDLINE, and Web of Science databases for articles published from January 2013 to August 2018. Two reviewers independently screened titles, abstracts, and full-text articles that reported using GG in GME and assessed the quality of the studies. A systematic review of these studies appraised the literature for descriptions of its utility in GME. Results Following our search and review process, 37 studies were included. The majority evaluated GG in surgical specialties (n = 23) for the purpose of surgical/procedural skills training or supervision. GG was predominantly used for video teleconferencing, and photo and video capture. Highlighted positive aspects of GG use included point-of-view broadcasting and capacity for 2-way communication. Most studies cited drawbacks that included suboptimal battery life and HIPAA concerns. Conclusions GG shows some promise as a device capable of enhancing GME. Studies evaluating GG in GME are limited by small sample sizes and few quantitative data. Overall experience with use of GG in GME is generally positive.