I also wear a hat most of the time, Mostly because I'm bald on top!
and not by choice.

However I do own quite a collection of several style hats,American cowboy,Austrailian cowboy(different from American) ball caps, stetson fedora and my bonnet that I wear for re-enactment.(sort of a balmoral)

I enjoy wearing each and every one of them. But somhow I don't think a cowboy hat goes with a kilt. At least my wife doesn't think so

But I think that a military beret may look very sharp, I was in the Navy for ten years and I always envied that guys that wore the beret. They seemed to be some how more confident and professional.
and way cool the women always went for them more then just us regular guys.

Now if only I could get one for myself. MMMM maybe my friend in the army could get me one.