Background: The natural evolution of facial scars has not been well described. Identifying factors that correlate with optimal scar healing may help patients and physicians during the perioperative period. Methods: A retrospective study of 108 facial skin cancer patient scars was performed. The Patient and Observer Scar Assessment Scale (POSAS) was used to grade scars at two time points (1 week and 3 months postoperatively). Paired two-tailed t-tests identified differences in scar ratings between the time points. Analysis of variance (ANOVA) explored whether POSAS scores differed by anatomic site or reconstruction type. Receiver operating characteristic analysis was performed to identify if 1-week scar appearance correlated with scar appearance at 3 months. Results: Between 1 week and 3 months the total POSAS score improved by 36.3% and overall opinion of the scar improved by 38.6% (p < 0.001). Facial cosmetic units differed in their 1-week and 3-month scores and all anatomic sites demonstrated significant improvement between time points. Differential scoring occurred among reconstruction types. Scar appearance at 1 week was able to predict overall scar appearance at the 3-month visit (area under the curve = 0.7732). Conclusions: Early scar appearance predicts later scar appearance, and scars will improve by nearly 40% 3 months after surgery. These data can be used to assist with perioperative counseling and expectation management.