I have to admit that I’m a bit of a hat guy. I’ve got a fancy collection of regional headgear from around the world. Every hat says something about it’s culture, climate, and traditional profession. I recently saw this chart of pretentious hats and it does a good job of making the point: hats say something about your character.
Whether we start off in media res, in a tavern, or with a long exposition, every 0-th adventure always has a “describe your character moment.” Generally people say something about race, facial features, armaments, and clothing. Little attention is paid to the headgear unless it’s particular part of the character’s flair: i.e. the iconic Cavalier hat with large plume of the Muskeeter.
Without bothering to find evidence to back up my claim, I’m going to assert that most characters in a fantasy world are going to have their head covered outdoors. Whether it’s for a formal holy day, a helmet on the town guard, or something with a wide brim to protect oneself from the sun. Players should expect that their characters have a good shot at identifying a villager’s profession and economic status by their hat. A gold-rimemd toque on a bloke at the market? There’ s a good chance he cooks for the king. A clean, yet threadbare bonnet? She’s either a poor married woman, or a pickpocket disguised as one! Adventurers are easy to identify: they’re wearing protective head coverings, dented and bloody, even when there’s no expectation of being attacked.
It’s reasonable to think that a freshly built character’s hat will nicely match the ensemble, but what about once she starts acquiring head-slot items? Most magic hats are helms, circlets, or crowns. How would one of those fit in with the rest of her outfit? As far as I understand the rules, head items don’t count as armor, and so she can wear a steel, face-plated helm with cloth armor. I know the rules make an exception for this, but I’d probably laugh at someone wearing a big steel fishbowl with his street clothes. What about a crown? Europe’s fanciest crowns almost have a tangible magic where you can believe in their magic. But even those were worn only on special occasions: they’re too heavy, fragile, and valuable to wear while adventuring, yet that is what happens in D&D. Imagine how much attention a character would draw walking around the woods or a city with a big, fancy crown! What would the actual ruler think? And I think fancy hats would also be an attractive target for a grab & run (that would make an awesome monster power–see below).
Rule-wise I think what the item physically is isn’t as important as its slot, and so when making your wishlist of items for the DM, feel free to ask for a head-slot item that appears in a form better suited to your character’s appearance.
For inspiration here is Wikipedia’s list of hats: http://en.wikipedia.org/wiki/List_of_hats_and_headgear. And here is the hat-stealing power I just came up with. It’s for novelty purposes only:
Let me close with these immortal NWH lyrics: “Grab a brim, babushka, or yarmulke (Yo G, what about a bonnet?). It really don’t matter just put a lid on it.”