gwen There is one obvious solution here: be brave. Be a man, wear a dress. Normalize it for your peers and those who come after you.
That's true. Most people don't have the self-confidence they think they have. And only want to be part of "the group". So they laugh at people or bat an eye on them if they do something that isn't "normal". But if you confront them head on and they don't have the secure feeling of the other members of "the group" the laughing stops and the stammering begins.
And so you can change the thinking of people. If people see your are happy, self-confident and don't want to disabuse/convert them all day with your own believes, they just accept you and every thing is good.
And in my opinion this is the best way, if you want to bring the society to acknowledge and accept the wearing of chastity belts. But I know this is a very hard way to go, because you have to build this self-confidence for yourself first.
gwen Be a man, wear a dress.
I only wanted to point out with this, that the fashion industry is at the moment very limited when it comes to fashion for men. Just look at politician for example (in the western civilization), men always wear suits and women wear so many different clothings (suits, dresses, costumes,...). If you look some centuries back, there you can see that is also possible for men to wear more different kind of clothes, if they are politician.