None of my characters have worn a helmet in any Elder Scrolls game.
most of the time, yeah they do. I have a mod that adds armored hoods and crclets to the game so sometimes i use them if it fits the character better than the helm (like a Battlemage or Heavily armored cleric)
Very rarely will any of my characters wear any sort of headgear. TBH, I can't even remember the last time one of my characters had worn a helmet...hoods maybe, but not helmets.
I usually hotkey them and only wear them in combat.
I find quite a few of the game's helmets to be hideous, so not often.
Anything with goofy horns sticking out of the sides that can easily be flipped off is a no-no for me. (Stalhrim is especially hideous)
Only when my character needs the extra armor protection. Otherwise I wear enchanted circlets.
One of my mods lets you wear circlets and hoods (it's a mod doing that right?) So i wear that one crown that gives you another standing stone slot, under a hood.
Otherwise, it's what goes with the rest of my armor.
I'm vain and like to check out my character every now an again so if I'm not in combat then no helmet for me.
M'aiq only wears his hooded robe with matching boots, but M'aiq longs for a Colovian Fur Helm. Practical, yet stylish. M'aiq is very sad he does not have one.
My male PCs, yes. My females, sometimes, but prefer a circlet for them.
Not in towns, most of the time, and not in my house. But in the wilderness or inns, etc, yes.
Never.
<- My character always wears this funny hat even with armor.
Edit:
It's much more fun to wear what you want and not be forced to wear full armor in my opinion. With all armor pieces the game would become easier and I'd have to increase difficulty level.
This is a general answear for all games I play.
It depends on what kind of character I play.
A knight in full plate suite, sure, it would be strange not to wear a helmet.
For a mage? Eww.. But if there is some kind of fancy headwear/circlet or whatever I could sport that.
Thieves, not helmets but often hoods or similiar.
My current character, a vampire I play. No, but she doesn't wear any armour either. Just miner clothes, a pair of boots and gloves. Think I snagged a necklace from someone as well.
those that covers the entire face - never
those that are open faced like nordic carved - sometimes but extremely rare
overall - rarely
Some wear helmets , some prefer dragon priest masks. Only my pacifist Nord wears a circlet.
I used to avoid them, but since Skyrim and the perk I wear them whenever exploring or in battle. I even wear them more in previous games like Oblivion or Morrowind now.