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Aim Lipedema is a chronic, progressive disease that predominantly affects women and is strongly influenced by estrogen. Its onset or worsening is associated with hormonal periods such as puberty, pregnancy, pregnancy induction, and menopause. It is characterized by abnormal, bilateral fat deposition in the buttocks and legs, which may be accompanied by edema, pain, and tenderness to touch. It is still frequently confused with more common conditions such as obesity and lymphedema. Pycnogenol® is a combination of anthocyanins and phenolic acids belonging to the large polyphenol family, with potent antioxidant activity and a proven effect in controlling chronic venous insufficiency. It has been used by several professionals for the symptomatic management of lipedema. Objectives This double-blind, randomized clinical trial sought to demonstrate the effectiveness of Pycnogenol® in the symptomatic control and body composition management of patients with lipedema. Methods This was a double-blind, randomized clinical trial with 60 days of follow-up involving one hundred patients. The study utilized a quality-of-life questionnaire (QuASiL), bioimpedance analysis, and clinical monitoring. Results Of the one hundred patients initially included, seven were lost to follow-up; however, monotonic multiple imputation was applied for data analysis. The two groups were similar in all aspects except for initial weight. The placebo group showed an increase in mean QuASiL scores after 30 and 60 days from the first assessment, representing a worsening of symptoms over time. In contrast, the intervention group demonstrated a progressive and significant reduction in scores, with means of 69.5 ± 28 at 30 days and 63.2 ± 27 at 60 days (p < 0.001). This group also showed a statistically significant reduction in weight, BMI, and body fat percentage. Conclusions Pycnogenol® appears to be a promising therapeutic option to support the clinical management of lipedema, a condition that exerts numerous negative physical and emotional impacts throughout the lives of affected patients.