I usually wear a hat of some kind, as my mind expands it's forcing my scalp up through my hair like a sand bar in a river. I wouldn't usually wear a ball cap with my kilt, but then again I wouldn't usually wear a ball cap at all. I think it looks fine on you except for the uncharacteristic stern glare it causes. It's not a uniform, if the hat and glasses are functional for you then wear them. I think you'll be just fine. I won't even tell Ham since we all know he detests headdress on principle.

Jamie