Cutaneous squamous cell carcinoma (cSCC) is the second most common non-melanoma skin cancer, and it accounts for 20% of all skin cancers. It occurs typically on parts of the skin exposed to sunlight and begins as firm erythematous papules or nodules that enlarge over a period of months in most cases. This study investigates the unusual presentation of cSCC with the goal of raising awareness of rare presentations and promoting accurate diagnostic tools. It is a five-year retrospective study retrieving patient data to study the demographic, clinical and histological features of cSCC with unusual presentations that were clinically unsuspected. It was carried out in Al Baha Province, southern Saudi Arabia. A total of 25 cases were included; males predominated (60%), and the mean age of the cohort was 59.8 years. However, three patients were <50 years old and the most prevalent site of the cSCC was the nose. Tumor size ranged from 5 to 50 mm with a mean size of 14.6 mm. Tumor size was uncorrelated with a clinical suspicion of malignancy. The clinical presentation of cSCC varies from tan nodules in most cases (28%) to warty lesions in 4% of cases; the clinical diagnosis of such lesions also varied from highly malignant lesions (melanoma) to a simple inflammatory disease. Histologically, most cases (96%) were keratinizing squamous cell carcinomas. A clinical suspicion of cSCC is not always accurate, and histopathology is the most accurate tool for diagnosis. Abdominal wall, perianal and finger sites are not immune to cSCC, and young individuals are also at risk.