not talking about character creation. I remember someone said that in oblivion they wore the mythic dawn robes the whole game just because of how it looks. My cousin always wears hoods no matter what class he is.
very much so, in oblivion I tended to pick the armour I liked the look of best, then enchant it so that it had good stats, additionally I tend to keep a set of normal clothes on me to change into when i'm in town or such
I like to walk around in some nice threads if I'm strolling through town and doing business. If I plan on getting into some trouble I do it in style with the nicest set of armor I can find or make. Looking good no matter what I do in Tamriel.
of course, in fact, in oblivion i mostly wore elven armour so i could wear an amulet that is visable (that big blue amlet from the girl in bruma, forgot the quest)