You're not suffocating your scalp by wearing a baseball cap or cowboy hat and you're not stifling hair growth—those are myths. Pattern baldness is linked to genetics, not your wardrobe.
Some people scapegoat hats by attributing baldness to poor blood flow to the scalp. True, some people inadvertently pull hair out of their follicles when removing a cap or hat, but such hair loss is negligible. If you're a cool dude in a cap, wear it.