Chichikov wrote:
My attitude to these things is that if you really hate what I normally wear then the relationship isn't going to work anyway, cos I'm not going to change how I dress for a woman.
If it was a nice restaurant I'd probably pick by better\smarter jeans and throw on a smartish shirt but that's about all. I know first impressions and all, but you don't want to set wrong expectations either. It will be important to her to know that if you do go somewhere smart that you recognise to dress yourself a little better than normal, but it's also important to let her know that isn't your usual style. I'd maybe bring it up as a conversation piece, "You look nice, do you normally dress like that, or more casual? I like to dress up for a nice restaurant but I normally prefer to wear <describe your usual style here>".
I have a very different attitude. I mean, I never really cared much how I look in terms of how I dress. So if I was into a woman enough, and her suggestions weren't too controlling, I'd basically look any way she liked me to. I'm not so prideful or set in my style to not compromise that part of me. There are areas I'd never chage (smoking weed) but clothes arent one of them.