Very sharp, Alex! I've got the Ian Grant site in my bookmarks and occasionally drool over their products; you're a lucky man with a beautiful crest.

As for keeping it vertical, you might try tucking a small piece of card inside the hatband (on the inside of the bonnet) and pinning it through both the hat and the card. I don't think you'd actually feel the card, but it should help to keep the pin upright.