Being a straight female, I don't know how useful my advice will be
, but you might try some of the Rhodok ladies: Lady Timethi, Claudora, etc. (their faces are repeated and there are several ladies with that face in the Rhodoks).
I found a horrible picture from the wiki
here, but trust me, they look better in person. Also, they look really good in hats and since whether they get a hat or not is completely random, at least you know that they'll look good whatever happens.
Some of the blonde Nord ladies look pretty cute, as well. Unfortunately, the Nord ladies sometimes spawn wearing wimples, which look horrible!
Anyway, on the rare occasions I play male characters, I scope out likely ladies in the beginning of the game while I'm riding around trading and setting up enterprises. Hey, I may be straight, but I'm also completely obsessed with aesthetics!
Oh, check out the Khergits, too: Khergit headdresses also look good no matter who's wearing them.