Background: The face, with its attractiveness, is positively connected with self-esteem and interpersonal relationships, and the maxillary central incisors are the most noticeable teeth and crucial for smile aesthetics. The aim of this study is to examine facial and permanent upper central incisors’ clinical crown dimensions and their correlations to establish whether there is a relationship between the length/width of the face and the length/width of the clinical crown of the permanent upper central incisors. Methods: This study included 100 subjects (43 males and 57 females) with a mean age of 17.5 ± 3.4 years before orthodontic treatment. Facial length and width were measured using a cephalometer by the same orthodontist and the upper central incisors’ clinical crown lengths and widths were measured using a sliding calliper by the same dental student. Data were analysed using SPSS version 29.0, presenting descriptive statistics for age, facial and upper central incisor crown dimensions, and indices. Pearson’s correlation coefficient assessed the relationship between facial features and the upper central incisors’ crown. The significance level was p ≤ 0.05. Results: Males exhibit a slightly higher mean value of the face length (11.6 ± 0.8 cm) compared to females’ face length (11.2 ± 1.1 cm) and a statistically significant (p < 0.05) higher mean value of the face width (11.7 ± 0.8 cm) compared to females (11.1 ± 0.6 cm). The facial index shows no statistically significant gender difference (males: 99.1 ± 8.4; females: 101.2 ± 11.9, p > 0.05). The upper central incisor crown dimensions are without statistically significant differences between gender and tooth side: males have mean value clinical crown lengths of 10.2 ± 1.1 mm (left) and 10.1 mm ± 1.2 (right) while females have 9.9 ± 1.0 mm (left) and 9.8 ± 0.7 mm (right). Clinical crown widths are also comparable (males: left 9.0 ± 0.7, right 8.9 ± 0.6 and females: left 8.8 ± 0.7, right 8.8 ± 0.7), with no statistically significant differences observed. The tooth index shows no statistically significant difference but there is a statistically significant (p < 0.05) correlation between the facial index and tooth index. Conclusions: Knowledge of the presented data is important for diagnosis and treatment planning and may be useful for restorative dentists, orthodontists, prosthodontists, and maxillofacial surgeons to achieve an aesthetic result. Clinically, our study supports the development of more personalized treatment plans.