To assess the trueness of digital measurements using direct and indirect scanning approaches compared to the actual clinical measurements. The crown length, width, and width/length ratio were measured in 36 anterior maxillary teeth using three different methods. The first was clinically using a digital caliper, the second was by scanning the teeth using a digital scanner and the third was by making an impression of the teeth, constructing a stone cast in the lab, and scanning it to obtain digital measurements. Bland-Altman test and intraclass correlation were used to assess the data and make comparisons. Measurements taken using both approaches were highly reliable, with intraclass correlations ranging from 0.934 to 0.977 (p ≤ 0.000). Bland-Altman plot reflected a minimal mean difference between measurements especially in crown width measurements. Crown width/crown length measurement displayed the highest mean difference. Both direct and indirect optical surface scans showed similar high trueness in linear measurements of teeth. A higher discrepancy was detected in the crown width/length ratio. Digital dentistry is the new era in patient management. The use of conventional impression techniques and physical dental casts is associated with several disadvantages. Scanning dental casts to convert physical records into digital ones has multiple advantages. Optical surface scans (digital models) of the dentition are currently being more broadly used and advocated in the different dental disciplines including the construction of surgical guides for esthetic crown lengthening procedures. The trueness and reliability of linear measurements are of paramount importance to allow for proper fit and predictable outcomes. In this study, the trueness of these linear measurements obtained using direct and indirect methods was compared to the actual clinical measurements.