my son in HS (early 2000s) wore skinny jeans...and he would have looked cute if he hadn't insisted on wearing boxers that bunched up over the top of them! never could get him to agree to that (he wasn't the only one though) it was a trend.
I wear skinny jeans, only because I'm pretty small and hate when my legs swim in the regular kind. however...if a guy my age was wearing them and not in shape...I think I'd be sad for him. trying too hard ya know?