Background: The objective was to determine if asymmetric facial features, nasal and chin deviations, affect the perception of attractiveness of a dental midline angulation, and if it is consistent among both dentists and laypeople. It was also analyzed if factors, such as the sex, age group of the participants and the dentist’s area of operation are relevant in their assessment. Methods: A cross-sectional study, approved by the Ethics Committee of Fernando Pessoa University. From a symmetrical facial model (SFM) image, a natural-looking asymmetrical face was created. Based on this asymmetric facial model six images were created, with different directions and degrees of inclination of the dental midline. In total, 236 laypersons and 242 dentists completed the online questionnaire where they rated the self-perception of attractiveness of the eight images (VAS scale from 0 to 10). Non-parametric comparisons (IBM© SPSS Statistics vs. 27.0, p < 0.05). Results: The results showed a significant difference in the perception of attractiveness between laypeople and dentists. This finding was consistent regarding every image, except for the SFM. The factors, sex of the people participating and dentist’s area of operation, seemed only to contribute to a significant difference in the perception when it came to the SFM. The perceived attractiveness of the images, for dentists and laypersons, did not differ by age group of the participant, apart from images 6 and 8. Conclusions: Dentists are more rigorous about dental midline inclinations than laypersons. The perception of attractiveness was affected by the age group and sex of the participants and the dentist’s area of operation.