They look a little sloppy. You can't express yourself through a T-shirt that someone else has designed. A black felt hat. A George Strait Resistol hat. It depends on the quality of the fur in the hat.
Straw hats are definitely less expensive.
It depends on the brand, the straw weave and water resistance. Start with boots and a cowboy hat. You just build up your wardrobe from there. I'm a mega window shopper. But I'm not a good window shopper because I usually buy something.