I've had problems with my ears when it gets cool too - and have thought I was nuts all these years. I finally found headbands at Target that work great - they're about 1 1/2 inches wide or so and work fine under my helmet. I put my sunglasses on over the outside, but they work just fine that way. I'll have to see what I need when the weather gets cooler - I've not had to deal with hats yet.