 How many cowboy hats can you wear? I had one on. How many cowboy hats can you wear? One a day, seven. I tell you what, just as I was reminded a minute ago, women, once they have a hat on, can never take it off. So that's sort of why you don't wear them all the time, because you just can't do without them. Once you plop them on your head, you have hat hair. Now, do you wear it inside, though, too?