This study aimed to determine the correlation between gingival stippling (GS) and other phenotypic characteristics. Adult subjects in need of CBCT scans and comprehensive dental treatment in the anterior maxilla were recruited. Facial gingival thickness (GT) and buccal bone thickness (BT) were assessed utilizing CBCT. Standardized intraoral photographs were obtained to determine keratinized tissue width (KTW), presence of GS in all facial and interproximal areas between the maxillary canines, and other variables of interest, such as gingival architecture (GA), tooth shape, and location. Statistical analyses were conducted to assess different correlations among recorded variables. A total of 100 participants and 600 maxillary anterior teeth constituted the study population and sample, respectively. Facial GS was observed in 56% of men and 44% of women, and it was more frequently associated with flat GA, triangular and square/tapered teeth, central incisors, and men. Greater mean GT, BT, and KTW values were observed in facial areas that exhibited GS. Interdental GS was present in 73% of the sites, and it was more frequently observed in men, in the central incisor region, and when facial GS was present. Multilevel logistic regression revealed a statistically significant association between the presence of GS and KTW, BT measured at 3 mm apical to the bone crest, and tooth type. This information can be used to recognize common periodontal phenotypical patterns associated with specific features of great clinical significance.