Chronic venous ulcers are a debilitating condition that often significantly impacts the quality of life due to their tendency to recur. Recently, we encountered a case of challenging chronic obstructive iliofemoral venous disease, presenting as postthrombotic syndrome with a venous ulcer. Venous duplex ultrasound revealed evidence of venous reflux in the left great saphenous vein and small saphenous vein. A CT venogram indicated occlusion in the proximal femoral vein, common femoral vein, and external iliac veins, with collateral veins in the lower abdomen. This lesion was treated using a combination of two types of venous stents. A one-month follow-up revealed improvement in the patient’s edema and ulcer.