I think the key to wearing hats with any length of hair is to make sure your hair peeks out from under your hat. With my short hair, I shove as much of my longer hair to the front as I can so that the longer bangs frame my face on the one side. If I tucked my hair under my hat or wore it pinned back, I think I'd have to wear a lot of makeup to compensate! With longer hair just make sure to have hair in front of your ears, at least on one side. Once again, don't tuck your hair behind your ears, and if you do, make sure it is only on one side. I've listed some of my favorite hats, at all different price ranges below. Don't be afraid to try this trend this year- its all about believing you can pull it off!