Well if we're staying local I'm usually content to get him to wear a CLEAN shirt when going out let alone tackling the "let's dress up issue" but he seems to have taken to Valentine's Day or New Year's Eve as holidays where a bit more of a dress up (dress shirt, pants & tie) would be okay. To get him in a suit/tux? Well, had to marry him to get my wish on that one! Although he has gone out and purchased a new suit to wear for our Mexican Riviera cruise. I begged, I pleaded, and eventually he decided he'd never see the people again anyway so what did he really care what he wore!
Maybe you'll have to invent some more "special occaisions" for yourself!