I probably have a bigger head that you, but sadly only in physical circumference. I bought this hat because I loved the fact that it combined two of the best inventions the hat world has seen together. I'm talking about corduroy and trucker. Yummy. Anyways I bought the hat and well, I have to pull it down really far on my head in order to make it look like I don't have a little puppy stashed up there. It is doable...but I think that is because I have the aforementioned giant head. If you have a smaller head and don't want to look like a mega-trucker then shame on you. Just kidding, but you could look ridiculous.