Background/Objectives: Rates of postoperative recurrence of varicose veins range from 7% to 62%. We analyzed factors associated with recurrent varicose veins (RVVs) of the lower extremities after interventional treatment. Methods: We enrolled 99 patients (114 lower extremities) with RVVs admitted from January 2018 to June 2025 (71 women, 76 limbs; 28 men, 31 limbs; average age (SD) 63.9 (9.8) years). Duplex ultrasound scanning, magnetic resonance venography, or computed tomography venography were performed. The presence of a residual great saphenous vein, primary deep venous valve insufficiency, incompetent perforating veins, and iliac vein stenosis were recorded. We analyzed the charts of patients who underwent operations for recurrent varicose veins for associated factors. Results: We recorded residual trunk of the great saphenous vein in 55 limbs (48.3%), deep venous valve insufficiency in 47 (41.2%), incompetent perforating veins in 7 (6.1%), anterior accessory saphenous vein insufficiency in 2 (1.8%), and small saphenous vein insufficiency in 2 (1.8%). Iliofemoral venography indicated 31 limbs (27.2%; left lower, 24; right lower, 7) with a nonthrombotic iliac vein compression lesion. After identifying associated factors, retreatments—high ligation and stripping of the great saphenous vein or iliac vein stent implantation or small saphenous vein dissection ligation and stripping—were performed. The venous clinical severity score was 7 (interquartile range, 5–10) on admission and 3 (interquartile range, 2–4) 3 months after discharge.Conclusions: RVVs are associated with multiple factors, including inadequate initial surgical techniques, nonthrombotic iliac vein compression lesions, deep venous valve insufficiency, small saphenous vein insufficiency, and incompetent perforating veins. Performing detailed imaging before retreatment is essential to identify factors associated with RVVs and prevent recurrence.