The chef's tunic and hat. Looks hilarious if wielding a knife and fork and taking on a dragon in 3rd person.
LOL
Started off with poor, common person clothes - especially liked the talsgar the wanderer type ones. Also wore a hat and gloves if I was up north where it's cold.
Then when my character got 'richer' and more well known, switched to the more finer clothes such as Jarl robes and such.
To be fair though, add a circlet to anything bar ragged robes and it makes you look like nobility.