Purpose Symptomatic large (>5cm) lipomatous lesions encompass a spectrum of benign and malignant entities. As biopsy is not always recommended due to malignant seeding, this study aimed to evaluate CT and MRI features, correlating histopathology to demonstrate utility and optimal choice of pre-operative imaging. Methodology A retrospective observational study was conducted at Werribee Mercy Hospital, Melbourne, between January 2021 and December 2024. 15 patients (10 male, 5 female, average age 53) with large lesions without concerning symptoms had CT (n=6) and/or MRI (n=9). Multidisciplinary discussion guided surgical excision decisions (n=10). Data was collected from medical records, radiology MDT discussions and histopathology reports. Imaging features analysed included lesion features, T1/T2 signal intensity and enhancement. Descriptive statistics and sensitivity/specificity calculations were performed. Results 15 lesions were analysed: lipomas (n=13), myelolipomas (n=1) and atypical lipomas (n=1). Benign lipomas were all non-enhancing on CT and MRI, while MRI was required for atypical lipomas exhibiting septations and irregular enhancement. Myelolipomas showed fatty components and nodularity on CT. MRI is recommended to exclude atypical lipomas, demonstrating high sensitivity (100%) and specificity (66.67%) in distinguishing benign from atypical/malignant lesions. Conclusion We suggest that all lipomatous lesions >5cm undergo CT, and preferably MRI if atypia or malignancy is suspected. Imaging features such as heterogeneous T1 signal intensity, septal enhancement, nodular/solid components, and irregular borders are critical for distinguishing malignant lesions, aiding diagnosis and guiding appropriate surgical excision.