Since I'm an older guy in the dating world, I receive plenty of advice and comments from women, both solicited and unsolicited, about what I should and should not be wearing. Jeans are not completely out, but they definitely are not the standard casual wear they used to be. I have cleaned out my closet and started over, and now have one pair of dark denim and one pair of black jeans. Both fit properly, which is the most important thing.
Loose, boxy jeans are definitely sending the same message as cotton sweats: you've given up caring. At this age, some of you have earned that, so do what you like.