Varicose veins are commonly due to saphenous vein reflux, but they can manifest more complex venous pathologies. A 45-year-old woman presented with painful leg varicosities and pelvic pain. Duplex examination showed bilateral superficial venous reflux, and, on further interrogation, cross-sectional imaging demonstrated enlarged ovarian veins and nonthrombotic iliac vein compression. Ovarian vein embolization followed by iliac vein stenting and bilateral lower extremity venous ablations and sclerotherapy was performed. After 5 years, she reports no pelvic symptoms and minimal leg symptoms. This case highlights the complex interplay of these venous pathologies and their successful treatment.