Call it a pet peeve in gaming.
I get really into a game, describe my character, get started and ask everyone what they look like...and I get "eh, I dunno. He's wearing armor and has a sword." That all so crucial into segment when I get to build a mental picture of the rest of the party is ruined for me. They become faceless NPC #1302. Ugh. You think I have issues with NPCs that don't have descriptions? Well...PC's with out also give me the willies.
I'm not mad at the player, but it does hurt the immersion for me. You have to understand, I suffer from the need to accessorize. I LOVE characters with cool costumes and outfits. I want to know about belts, tools, colors, and things like the way they carry themselves. Take a look at Dungeon World, each of the playbooks for characters has a short 3 little descriptive eyes, clothing, hair elements. It's WONDERFUL. Seriously every game book out there should have tiny advice for races, classes, just to help new players visualize and describe their characters.
I don't know if I'm infected with the latent writer, movie costume designer, or just the little kid wanting to play with dress up dolls. Maybe all 3. I just want my character to look unique enough to stand out.
So what does have to do with hats? Well, I commented on G+ that wizards are sexy in their hats and robes. And I stand by that. Something about a Wizard's hat, depending on the type is important to me. I know a lot of wizards do with out the hats and go for a crown, or head accessory less...but it feels wrong to me. I'm not just talking about the Gandolf here. I like the idea of fedoras, long sombreros, the dusty 10-gallon. Wizards need to have sexy hats.
It's a thing. It's my thing. But *ahem* I'm going to use it to show you a trick I use when describing characters.
Let us say I'm going to sit down for a session of GURPS Dungeon Fantasy and I've decided to play a specialist wizard. Maybe he's a Geomancer and specializes in reshaping stone and rock with a bit of engineering skill to make it useful deep in the dungeons.
Cool, I got the baseline concept of the character down, but how do I describe him?
Here is my quick and dirty method:
1. What is his Job?
He's an engineer caster, so his robes will have belts, look more like work clothes. Browns and light yellow or greens. Lots of pockets, and engineer tools, like say pencils and plumb bobs.
2. What is his wealth?
He's a professional. So I'll put him above most folks (must remember to buy some Wealth). So nicer leather belts, cleaner clothing well tended too. Still keeping in the idea of him being a pro so lack of obvious wealth, maybe a ring of his guild/college he trained at. Not much else.
3. What his personal outlook?
I'm going pure "Pro From Dover" here. When I say personal outlook I don't mean the generic stuff most books ask you. I'm asking what the outward impression I want the other players to have. Very much becoming the mirror here. So in my wizards idea, he's in his late 20's. Clean cut, maybe with a "work long hours" 5 O'clock shadow. Clear brown eyes, and just for flavor, reddish brown hair. Short cut. His hands look like worker's hands.
4. How intimidating is he?
No seriously, intimidation factor is BIG with roleplaying characters. In my character's case he's not very. He has the air of a calm engineer, but doesn't project much. So I'll describe him as homely and friendly. This is important.
5. How stylish is his hat?
VERY important for my Wizards. Now, my guy is a pro, but maybe this is his one accessory he spends some time on. I could be very technical about regional hats, etc. But I'll keep sane and say he wears a clean, crisp black tricorn hat with a stylish green feather in it. The hat has gold trim. It radiates, just a hint of pride and money. See how a good hat just makes the Wizard?
Now, the trick is those 5 questions are unique to my games. What you need to do is sit down and think, what are the 5 most important descriptive elements of my character? What 5 things do I care about in the way he or she looks? Then build those 5 costume/framing questions to guide your own costuming session. You might ask, What Kinds of Shoes does she wear? (Important to you) or, What sort of scars does he have? Or does she style her hair? Pick out the petty things that matter to you.
You see, IRL I have a large head and VERY, VERY few hats fit me. So for me roleplaying characters with a stylish hat IS pure pleasure. I find taking the time to fill in these details makes or breaks my enjoyment of a character in a game.