Background: In the context of guided surgery, augmented reality (AR) represents a groundbreaking improvement. The Video and Optical See-Through Augmented Reality Surgical System (VOSTARS) is a new AR wearable head-mounted display (HMD), recently developed as an advanced navigation tool for maxillofacial and plastic surgery and other non-endoscopic surgeries. In this study, we report results of phantom tests with VOSTARS aimed to evaluate its feasibility and accuracy in performing maxillofacial surgical tasks. Methods: An early prototype of VOSTARS was used. Le Fort 1 osteotomy was selected as the experimental task to be performed under VOSTARS guidance. A dedicated set-up was prepared, including the design of a maxillofacial phantom, an ad hoc tracker anchored to the occlusal splint, and cutting templates for accuracy assessment. Both qualitative and quantitative assessments were carried out. Results: VOSTARS, used in combination with the designed maxilla tracker, showed excellent tracking robustness under operating room lighting. Accuracy tests showed that 100% of Le Fort 1 trajectories were traced with an accuracy of ±1.0 mm, and on average, 88% of the trajectory’s length was within ±0.5 mm accuracy. Conclusions: Our preliminary results suggest that the VOSTARS system can be a feasible and accurate solution for guiding maxillofacial surgical tasks, paving the way to its validation in clinical trials and for a wide spectrum of maxillofacial applications.