Acroangiodermatitis is an uncommon, benign vasoproliferative entity that often develops in the setting of long-standing venous hypertension or arteriovenous abnormalities. Its clinical resemblance to other dermatoses often results in misdiagnosis and delayed treatment. We describe three cases, two males and one female, who presented with persistent lower limb lesions. Clinical findings included hyperpigmented plaques, indurated plaques, and erythematous soft nodules localized to the legs. Clinically, varicosities were evident in two of the three cases, and one patient had previously undergone surgical vein stripping for the same. Given the chronicity of lesions, biopsies were performed. Histopathological features were consistent with acroangiodermatitis, while dermoscopy showed vascular patterns along with white, structureless areas. Venous Doppler ultrasound confirmed the underlying venous insufficiency in all three cases. Based on clinical, dermoscopic, histopathological, and radiological evaluation, a final diagnosis of acroangiodermatitis of Mali was made. The patients were started on oral calcium dobesilate and topical corticosteroids and were referred for vascular surgical evaluation. This case series highlights the importance of recognizing the diverse and atypical presentations of acroangiodermatitis of Mali, emphasizing that biopsy and dermoscopy are critical for a definitive diagnosis.