This is an interesting thread.
It's summer here and DH is wearing shorts. Nice shorts, knee-length adult shorts.
GOD HE LOOKS SO FIT!
He's got lovely, lovely legs. I mean, seriously, I don't mean to brag. But those legs! And I make appreciative remarks quite a lot and jump his bones quite a lot and tell him he looks lovely, and yes it's partly because until he moved to this very hot place he'd not worn shorts much and was worried he'd look silly, and so it's always good to hear when you're looking good, right?
But if he'd said, "no, I don't feel comfortable in shorts" I wonder if I'd have said "but I want you to wear them for me." ..... I do hope not.
that said, I used to hate wearing dresses and now I quite like them. The key, I've found, is to wear something like bloomers, to stop my massive thighs rubbing together and getting hot. So I quite light wearing summer dresses over light leggings or something, if I'm fancying myself up a bit. But I dress for me, with one eye on looking nice and presentable to The World Out There, with DH at the top of that list.
I dress for me. Dressing to please others first and foremost seems like an uncomfortable thing to do.
Erm. I'm not sure what I'm trying to say here, OP, except that did I mention my DH looks great in shorts, and also, I think you should wear what you like :)