Background: A multitude of parameters influences the smile of a person. Individuals with pleasant smiles are often construed to be easily approachable. Aim and objective: This study aims to analyze the dental, facial, and gingival characteristics associated with confidence in smiling in the general population of Chengalpattu. Materials and methods: A cross-sectional questionnaire study was conducted in the general population among individuals from 18 to 50 years of age (N = 175) after required history elicitation and clinical examination. Independent samples t-test was used to analyze the self-perception about the beauty of teeth across gender. Results: A positive correlation between dental health status and confidence in smiling was found (p < 0.05). There was no significant association in the perception of study subjects regarding the beauty of teeth and liking toward their own smile across gender (p > 0.05). The parameters that were chosen the most by the individuals who wished to have a better smile were the alignment of teeth (n = 43, 16.6%) followed by teeth shape (n = 35, 13.5%) and teeth color (n = 32, 12.4%). Conclusion: Self-perception of the smile has an impact on the psychosocial well-being of the individual as well as confidence during smiling. Clinical significance: Understanding the perception of the general population about dentofacial features and their effect on an individual's confidence is of paramount importance for dental practitioners to provide better esthetic and functional results.