My boyfriend would like me to dress less "old" -- he can't seem to say what it is that IS OLD but he knows he doesn't like what I do. It's a struggle for me because I tend to be more classic style (cardigans) and that's just "old"
He would like me in more girly/revealing clothes but I'm not very comfortable in them. I struggle a lot with body image (was 300 pounds for a long long time and then lost over 150 of it) so that makes it doubly hard for me.
He will tell me if he doesn't like something but that's pretty rare overall. I find his opinion interesting because it's the oddest things he doesn't like.
My uniform tends to be dark jeans, a plain top (in gray, black, blue or a teal variant) , usually long sleeve since I'm always cold and cardigans, sweaters, shawls and scarves are a part of my attire. I live in Seattle so it's usually icky. I rarely wear skirts or dresses. I work at home so I don't need to dress up in any way. I'm a dansko clog wearer though have become very attached to my ballet flats, I used to think they made my legs look shorter/fatter so wouldn't wear them but I've come to terms with them
Anyway, I dress old. That's his big complaint. I do bear that in mind when I shop and try to find current clothes and he notices and pays compliments when he likes it. The other day I got a "you look really nice" when I was wearing what I usually wear .... so that was odd
But yeah, it's a balance ... they see what we don't see and sometimes that viewpoint is important. But I can't obsess about it or else I'd go crazy.