Cutaneous surgeons frequently evaluate and manage soft tissue tumors arising on the head and neck of adults. Of these, the most common tumor is the lipoma, and specific mesenchymal variants of lipoma occur classically on the head and neck. We describe a case of a large spindle cell lipoma of the posterior scalp, in order to highlight the classic location and differential diagnosis of the lipoma variants presenting commonly in this anatomic region. In addition, we review the role of preoperative imaging studies of scalp soft tissue tumors and discuss how imaging may assist the dermatologic surgeon in establishing the diagnosis and designing a rational surgical approach.