Pleomorphic fibroma (PF) is a benign, polypoid, or dome-shaped cutaneous neoplasm with cytologically atypical fibrohistiocytic cells. We describe the cytomorphological features of PF retrospectively with histopathological diagnosis in a 38-year-old male who presented with 3 × 1.5 cm swelling in the soft tissues of the thigh for 6 months. This lesion is benign despite the presence of pleomorphic or bizarre cells. We review the differential diagnosis of PF with other mesenchymal tumors. To the best of our knowledge, cytomorphological features on fine needle aspiration cytology of this tumor are not yet documented in literature.