Not that a stag-do is something I have to worry about at the moment, but I had an idea for an all-boys night out/opportunity to dress.
I was thinking that for a big night out you could suggest a 'dress up as a lady' theme to your buddies, and they might go along with it, but they'd probably half-ass it, go for laughs and thereby make you stand out more as 'taking it pretty seriously'.
So, what you could suggest is, everyone gets dressed up, then you rate each other, and the least convincing lady gets the first round in. Then the next-least convincing, and so on...
(I probably wouldn't use words like passable for fear of saying too much!)
That way, you could go out, all glammed-up for a laugh with friends (friends you might not ordinarily dress with) and put all the effort you've put in to looking pretty down to your competitive male nature!
Plus, if there were enough of you (and you were the most beautiful), you might get all of your drinks bought for you! lol
An unlikely, unrealistic, fanciful notion, but the idea makes me smile.