Objective: The aim of this cross-sectional observational study was to assess undergraduate dental students' esthetic self-perception of their own smiles. Materials and methods: A questionnaire consisting of two parts was distributed to 1400 dental students at all levels of study in the city of Riyadh. The first part was intended to measure students' self-perception of and satisfaction with their own smiles. In the second part, students were asked to rate the importance of specific features of an attractive face on a 100-mm visual analog scale (VAS) bar. Results: The overall mean satisfaction index was 9.32. The participants in the intern group were the most satisfied with their smiles. The female students showed more dissatisfaction than the male students with their smiles. Among the facial features important to facial attractiveness, teeth scored the highest (86.54) on the VAS, and the rating of this feature increased in relation to academic progress. The ratings of female participants were higher than male participants for most facial features. Conclusion: Although the results indicated an overall negative esthetic self-perception among the dental students, their self-reported satisfaction with their appearance increased as they progressed academically.