Would it bother you if a guy you were dating had a really casual style? Say the guy was actually quite rich, but chose to dress in a really casual way, like old looking t-shirts/ old looking jeans/ or cargo shorts/ flip flops etc.
I like a little bit of both. I like casual, definitely, a lot more than dress-up, but I also want him to know how to dress himself appropriately should we go somewhere nice. But mostly, whatever he's comfortable in I'm down with it, because I expect the same courtesy from him. Sure, I like to dress up, but I don't want to spend an hour every single day making myself polished and shiny, and I don't expect him to, either.
I like worn looks. I mean.. Clothes that are all brand new or you know, that shiny and very neat, they don't look cozy. The more casual the look, the more I'd like to cuddle him hehe :) I think it gives out kind of warm vibes.
If I went on a date with someone and used a lot of time to smell good and look presentable, and he ends up coming like you described I would be a bit frustrated, almost like telling me you could care less.