Background: Aneurysmal fibrous histiocytoma (AFH) is a rare variant of benign fibrous histiocytoma characterized by fibrohistiocytic spindle cells, blood-filled pseudovascular spaces, and hemosiderin deposition. Clinically, it may mimic vascular or melanocytic lesions, posing a diagnostic challenge. We describe the clinicopathological features of 18 cases of AFH and discuss its differential diagnosis. Methods: Archival records from a tertiary institution were searched for cases diagnosed between January 2009 and December 2021. Hematoxylin and eosin-stained sections and immunohistochemical preparations were independently reviewed by two soft tissue pathologists, and clinical, histopathological, and follow-up data were systematically analyzed. Results: The 18 patients had a mean age of 37.1 years (range, 14–64 years), with a slight male predominance M:F = 5:4 (10:8). Preoperative diagnoses were documented in 7 cases (38.9%), most commonly hemangioma (n=3). The back/scapular region was the most frequent site (33.3%), followed by the lower limb (22.2%). Grossly, lesions demonstrated a solid-cystic appearance with blood-filled spaces. Histologically, non-endothelialized blood-filled spaces were surrounded by bland spindle and histiocyte-like cells, most commonly arranged in a storiform pattern (55.6%). Mean hemosiderin deposition was 40.6%. Atypical/monster cells and Touton giant cells were each identified in 35.3% of cases, collagen trapping in 52.9%, and staghorn vessels in 23.5%. Resection was performed in 72.2% of cases. Among 12 patients with available follow-up (4–20 years), local recurrence occurred in 2 (16.7%). Conclusions: AFH can closely mimic vascular and melanocytic tumors. Recognition of its characteristic histopathological features, supported by targeted immunohistochemistry, is essential for accurate diagnosis and avoidance of overtreatment.