Back when it was snowing and I put a hat on Trey he would pull it right off. He recently figured out how to put it on himself. Since it is HIS idea now, he will wear it for hours at a time. He doesn't seem to notice that it is NINETY DEGREES out now and a hat isn't necessary. He hasn't figured out the sunglasses yet. Whenever I put them on him, he pulls them off instantly. (Have you seen him squint?) As soon as the weather turns this fall, he will master the sunglasses and wear them all winter.