Pleomorphic adenoma, also known as benign mixed tumor, is the most common salivary gland tumor, mostly affecting major salivary glands, but also encountered concerning minor ones. The occurrence of this lesion in the skin, known with the term chondroid syringoma, is unusual and considered to be associated with eccrine or apocrine glands. The two lesions demonstrate almost identical histological features with microscopic characteristics of both epithelial and mesenchymal origin. In this article two cases of benign mixed tumor of the lip are presented and their surgical management and histological features are analyzed. Both cases involved the upper lip, one was located in the subcutaneous tissues and the other in the labial mucosa. The proximity of eccrine sweat gland tumors of the skin with the salivary glands of the oral mucosa makes it often difficult to discern the origin of benign mixed tumor. This report discusses the particular characteristics of each pathological entity, the clinical differential diagnosis and the treatment approach chosen accordingly.