Patients with venous anomalies are at increased risk of developing venous thromboembolism (VTE) and subsequent complications, but they are often under-recognised. While unprovoked VTE may trigger testing for inherited thrombophilias and malignancy screening, anatomic variants are considered less often. Venous anomalies increase the risk due to venous flow disturbance, resulting in hypertension, reduced flow velocity and turbulence. Recognition is important as endovascular or surgical intervention may be appropriate, these patients have a high rate of VTE recurrence if anticoagulation is ceased, and the anomalies can predispose to extensive VTE and severe post-thrombotic syndrome (PTS). In this case series, we present representative cases and radiological images of May-Thurner syndrome (MTS), inferior vena cava (IVC) variants and venous aneurysms, and review the available literature regarding optimal diagnosis and management in each condition.