Purpose: To examine if there are differences in smile esthetic evaluation scores by orthodontists and prosthodontists and if there are changes in those scores when two evaluations are performed, when the time of observation is increased, and when the lips are present or absent from the images. Materials and Methods: In total, 12 individuals participated in this pilot study. Two digital images were taken from each individual. The first digital image was a smile view, and the second image was an intraoral view. Two presentation files were prepared, with two images for each individual. The smile and dental attractiveness ratings were obtained from 10 specialists. Results: Repeated measures ANOVA was applied including all four within-subject factors, the evaluator (E), the repetition (R), the time of observation (T), and the presence or not of lips (L). Factors E, T, and L each had a statistically significant main effect. E and R had a statistically significant combined effect. In particular, the esthetic score for the view with smile was overall higher than for the intraoral view. The same results were obtained when the analysis was repeated with the 10 evaluators grouped to prosthodontists and orthodontists, and the prosthodontists tended to score higher than the orthodontists. Conclusions: The evaluator and the presence of lips have a statistically significant effect. The present pilot study has found that three (E, L, R) out of four factors (T) are important for the evaluation of dental esthetics.