We also always over pack and I do not mind as long as my suitcase is 50 lbs or below and I have room for extras to take back with me.
I would rather have enough clothing than not enough and really do not want to have items dry cleaned while there. Being over prepared is better than wishing you brought something and left it at home. We love bringing the refillable cups for drinks at the pool bar. They are larger than the cups drinks are served in on the resorts and keep your drinks cool.