Background: Digital diagnostic waxing is a contemporary alternative to the conventional wax-up method. This study aims to evaluate the impact of both techniques on the perceived frontal symmetry in aesthetic treatment planning. Dental symmetry significantly influences smile perception and, consequently, the acceptance of treatment outcomes, highlighting its clinical importance in restorative dentistry. Materials and Methods: A total of 100 teeth were measured, with 50 (n = 50) waxed up using traditional modeling techniques and 50 using a face-guided digital approach. The study involved ten patients requiring fixed restorations in the aesthetic zone. Both digital and conventional wax-ups were performed for each participant. Gypsum models with wax-ups were digitized and superimposed onto the digital diagnostic design using 3Shape Dental Designer Studio software, Version 2023 (3Shape, Copenhagen, Denmark). Screenshots of the frontal view were captured, and the width of each morphologically altered tooth was measured using ImageJ software Version 1.54 (National Institutes of Health, Bethesda, MD, USA). Results: The results indicated no statistically significant difference in symmetry between the right and left sides achieved by the two diagnostic approaches (t-value = −1.89, p-value = 0.07). The perceived symmetry of morphologically modified frontal teeth, as achieved by digital and conventional waxing, was found to be comparable. Conclusions: Digital diagnostic planning is validated as a reliable alternative to the conventional wax-up method, offering comparable accuracy in achieving dental symmetry while potentially enhancing efficiency and precision in the aesthetic treatment planning process. This result underscores the potential of digital technologies to streamline clinical workflows and improve patient outcomes. Clinically, achieving symmetry in the aesthetic zone is crucial for patient satisfaction and acceptance of restorative procedures, emphasizing the need for continued integration of digital tools in dental practice.