Background: Periorbital melanosis (POM) describes the light-to-dark-colored, brownish-black pigmentation surrounding the eyelids. It can affect an individual’s quality of life. Dermoscopic features of POM are not frequently reported in the literature. Materials and Methods: This study comprised 100 patients aged above 16 years, who attended our outpatient department (OPD) from November 2018 to October 2019. A detailed history, clinical features, and the dermoscopic study of color, pattern of pigment, and pattern of the blood vessel were recorded with the Dermlite-3N dermoscope (3Gen, San Juan Capistrano, California). On the basis of the eyelids’ pigmentation and involvement, patients were clinically graded as Grade 0 to 4, with 4 being deep dark color extending beyond the infraorbital fold. The clinical patterns and the dermoscopic features were correlated. Results: Most patients were women (76) and the common age group was 16–25 years. Most of the patients had both the eyelids involved (58%), followed by lower eyelids (28%). The majority of the patients were having POM of grade 2 (47%). Seventeen patients (17%) had a positive family history of POM. The most common clinical form of POM observed was constitutional type (77) followed by postinflammatory type (12). Of 100 patients, 52 had pigmentary, 15 had vascular, and 33 had mixed pigmentary-vascular pattern. Cell phone usage (>4 h) and refractory errors (38% each) were the common risk factors observed. Stress and respiratory allergy were significantly associated. In the pigmentation patterns, epidermal (54%), dermal (14%), and mixed (17%) subsets were observed. The reticular pattern was the most common vascular pattern (65%). Conclusion: POM is a multifactorial entity. Multiple risk factors play a role in the pathogenesis and aggravation. Clinical forms did not show any specific dermoscopic patterns. Dermoscopy of POM helps to know the underlying pathology, which in turn paves the way to the effective treatment.