Most of the time I travel with two items, a carry-on and a personal item. They are both max for what is allowed but not over. I would not travel with something that is over the allowances as I do not want to have to check items (no fee for me but I want to walk off the plane and roll). If you do, you can get away with it but no guarantees. You should be prepared for the airline to tell you they have to check it.