I RP, too

Different suits for different characters and situations.
Dunmer mage: spooky full black robe. I think it has an enchantment on it or something, like Magicka regen.
Redguard merc: high quality Hide armor, boots, and gloves for traveling. When she goes into a dungeon, she suits up in full Orcish.
Bosmer archer: full Forsworn armor except no headdress. She is a wild child. Never wears anything else.
Breton spy: half a dozen different outfits, almost all just normal clothes with no armor value. My favorite is the Chef's Hat and Chef's Clothes. A close second is Hammerfell Garb with Redguard Boots. Thieves' Guild Armor for dangerous or "professional" jobs. She will often wear the Chef's Hat with other outfits; it's kind of become her trademark.