I'm a no-nonsense orc with a big set of armour and a hefty mace and shield(oh, how I love the Knights of the Nine), but I'm in the Dark Brotherhood, so I know my stuff in sneaking, too, it being a very useful skill
My older brother used to have a wood elf vampire with the Dark Brotherhood robes you get part way through, he didn't have to repair them at all, because they didn't count as armour! But when I tried, I had a nice little sword as back-up as well, but I still got a fair dosage of pwnage : (