I'm playing 4 characters now:
1) Imperial warrior with magic: Currently she's wearing the Wolf Armor. I like her in it and she may remain in it for the rest of the game. It seems to fit her character (she is the Harbinger after all)
2) High Elf - mage: Currently in Adept robes: I like them better than the black or blue robes - they're not floor length. Those just strike me as constricting. She'll probably end up in some sort of tricked out monks robe
3) Khajit Assassin - he looked silly in the DB armor so he sticks with leather and will probably stay that way until he can get a dunmer outfit and trick it out with one of those Alik'r hoods.
4) Breton Battle-mage - currently in ebony but going for dragon (intimidation factor!)
To me the outfit is very important.
Some suggestions
One #2 save some of the Vermina (or whatever it is) robes you get doing the dawnstar quest to get rid of the nightmares. They are the purple with the lighter purple tribal on the shoulders.
#3 maybe the thieves guild armor. Only thing that sucks about that is you can't get a regular outfit to enchant to your liking.
#4 IMO Deadric armor is more intimidating. Also don't forget the Nordic armor with I think looks cool wiht the bear helmet