For me, it's always about the aesthetics, but my characters decide, I don't have much say. Sometimes we disagree.
Ha! There is counseling for that... (for your character, not for you)
Same. I hate most of the helmets so I take the armor rating hit and use circlets or hats if anything.
Also why I mostly only use Annekke. Since her starting armor is basic clothing, she'll wear pretty much any armor you give her.
Same here. Most helmets look awful.
Lately, I am using blades armor with Zahkriisos. My current character loves using shock destruction at the moment, so Zahkriisos fits my RP and looks pretty good with the blades armor. Pluss it is Heavy so I get my perk bonus for having the whole set of heavy. Sometimes I switch to the circlet to get my 100% destro cost reduction if I am in the mood.