Coexistence of the Poland syndrome and gynecomastia is a rare condition. Poland syndrome requires soft tissue augmentation of the affected side, whereas gynecomastia necessitates reduction of the breast tissue. To provide symmetry, breast reduction and fat grafting techniques should be combined. We report a 29-year-old male patient with left gynecomastia and right sided Poland syndrome. In order to correct his asymmetry on the anterior chest wall, left breast tissue resection and fat grafting to the right breast were performed. Having these two opposite conditions at the same time and on the same patient makes the deformities look more dramatic than they are separately. Accurate planning and selection of proper techniques enable to provide symmetry in such cases.