I've completely forgotten where I read it but the most convincing sociological explanation for old school secret society cross-dressing I've heard was along the

I've completely forgotten where I read it but the most convincing sociological explanation for old school secret society cross-dressing I've heard was along the lines of: 1. These are cultures with very conservative ideas about gender and gender roles. Someone who cross dressed in their regular life would be shamed and excluded. It's considered degrading. 2. Since it's such a "bad" thing to do, when you are with your other high status peers it signals status to confidently do it anyway, as a joke only, to show that you are so confident in your position that you can even get away with cross-dressing. When you live at an extreme the normal status rules apply less and less to you, while the middle class engages in conspicuous consumption for status reasons, the upper classes can engage in conspicuous anti-consumption for status reasons. When you are high status enough, you can just ignore the normal rules because you are so comfortable and confident in your position. And this fact is something to show off with conspicuous rule breaking.