Probably discussed a hundred times but I haven't found a recent similar topic, so here we go...

what do your characters like to wear? Plain clothes, light / heavy armor, mixture of both or are they mostly naked? Do they use the same outfit all the time or change them according to regional temperatures (Jeralls vs Blackwood for instance) and do they use the same apparel for cities and adventuring? Do they wash their outfits or prefer them dirty? Do they repair their armors only when in towns / blacksmiths or anywhere?

I'll start... Falador prefers Unarmored (thanks to Galerion's mod this is a skill), meaning he usually wears some shabby clothes (preferrably combination of shirt + trousers, not robes) and a piece of light or heavy armor - currently iron boots. He wears hood at all times, except in Jeralls he was wearing an enchanted fur helmet. He washes his clothes on some rare occasion but most of the time he doesn't care if his clothes are dirty, ragged, bloody or falling to pieces as long as he feels comfortable in them. When they get too damaged (at least in my RP imagination), he changes them for something else, the only exception being his hood which he took from a first necromancer he came across and still didn't change it. His current outfit is necromancer's hood, dark green shirt, blacksmith pants, iron boots and two rings - base ring of Aegis and Namira's. He uses the same outfit for adventuring & visiting cities, the only exception when he was wearing something more noble was when he attended the party at Summitmist manor - there he was wearing Deceiver's finery (black & burgundy outfit).

In Ha wears a dirty grey robe in town, he is but a humble knight, and calling attention to himself in town, seems, obnoxious.
Heinrich's Shirt and Pants. Nuff said. That is the best overall outfit for my knight as he lounges on the deck at White Stallion Lodge.
When he needs to administer a beatdown, it is currently a Steel Cuirass, Leather Boots, Legion Greaves, Skyrim Gauntlets (found these in loot!, Resist Frost 7 %)
He wears a Green Robe Hood when it rains, and no helmet during battle. He wears his trusty Fur Helmet when visiting friends at the Bruma Guard. Brrrr!
He tries to wash his clothes as often as he can out in the wild. No one wants to be stinky.

The major factor is that this is one of my character's rules: He cannot repair items unless he is safe and in town or a settlement.
At Novice level armorer, he is allowed one tap of a repair hammer out in the wild, at Apprentice, two taps, and so on.
This leads to a lot of dropped broken armor and weapons. (dropped in dead ppl or animals for clean up) So often, on the return journey, my character is wearing something completely different, which tends to be a mixture of clothes and light armor, something he is not skilled in at all. Which makes for a nice challenge. He tends to use magical weapons and armor sparingly for this reason.