Maybe some guys do but I don't care how my fiance dresses. As long as she's comfortable, I don't care what women's dress, skirt, shirt, socks, shorts, or anything else she's got on. How can I tell her to stop asking me what I think? It gets irritating after awhile...sometimes that question turns into a half hour discussion and I want to shoot myself.
Sometimes they just wanna hear it cause they want to be confident on themselves and if you keep on just showing her and telling her even when she is not asking she will eventually stop and she would have gained a lot of confidence and excitement to wear just about anything and once in a while tease her on what she is wearing then see how she stops bugging you with that question.
Listen to me . . . she will NEVER stop asking your opinion on her dress. She likes to be reassured that you think she looks nice, but of course, you could be the only other ear available to her. Don't be subjective when she asks -- be pragmatic. Tell her if you think her clothing looks good on her, not whether you like it or not. My wife recently bought a shirt at a store, and asked me how it looked. It just didn't look good on her. It was a cute shirt, but it wasn't very flattering, and I told her as much. She appreciated my comments, because she wasn't completely convinced that the shirt looked good on her, which is why she asked me in the first place. She ended up taking the shirt back.
Dude you gotta understand women, are so worried about how they look, and in their minds they think they aren't. Don't ask me why that is, that's just how it is. When she says how do I look, what she is really asking you, is do you still think I am pretty. And when you say I don't care you look fine, that's not going to be taken lightly to her, she keeps asking you because she wants you to compliment her.
So next time she asks you, look at her then walk up to her put your hands on her waist and pull her close to you and say you look extravagantly beautiful in that dress and even in a pair of sweat pants, I don't want any other woman, she might then say no I am not that pretty, this is a trick by the way, so then kiss her and say you know your the most beautiful girl I have ever seen. And there you go problem, it may sound lame and dumb to you, but not to a woman she will love it and that my is what she wants to hear from you.
It's not something that's going to stop, and I don't think it would hurt you to actually think about it instead of resenting it every time the question was asked. Just tell her what you think, for a start, then work your way up to telling her what she wants to hear (if she notices the change, just tell her that the older she gets, the better she looks in everything.)