Originally Posted by AppAdrian
I don't see what's so silly about them. I personally don't fedora type of hats. And that was a pretty rude comment to be honest.
Somebody on the internet thinks ever single thing I like or want to do is silly, and a reasonable number of people in real life do too. I don't usually let it stop me. I mean, wear what you like, but if you ask for feedback on something you have to be prepared for harsh feedback. Similarly, of course, those who would give harsh feedback should at least try to be helpful, and to have a sense of humor. I realize that may not have come through, and if I didn't strike that balance, I apologize, but don't retract the core of my statement.
Anyway, you're going to be getting very square, very traditional advice on this side of the forum. The SWD side probably doesn't really go in for chauffeur caps, either. I think, if you're sold on the "statement hat" thing, you may get useful feedback on your idea over on the Fedora Lounge, where the idea that a bold, attention-getting hat is a good idea is a firmly-entrenched belief. I think most of the folks on this board will try to dissuade you from wearing a hat that will attract a lot of attention, unless everything else you're wearing is equally bold, and stylistically in keeping with the hat.
I don't think it's a great idea for me, a total layman, to stake a claim on whether something obscure is or isn't illegal, and given that the information you're looking for could potentially differ from area to area, you may want to look into it on your own. Probably your area's legal resources are a much better source than SF.