I'm behind the cause here. I generally like wearing clothes, but I hate that I have to and that there isn't a smooth landing if I was feeling frisky today.

In a free society these things will be handled in a decentralized way. People will judge you (rate you, whatever) based on whatever they find appropriate, and a norm for that community can develop.

And of course different communities can have different norms, and people will generally live around other people who share their preferences.

When we (voluntaryists) oppose clothing laws, a lot of people will think that's the same as being a nudist. But really that's not at all the case. Personally I might like that, but even if you have a very strict preference, voluntaryism is the only way to actually get that. Because as you point out, when you have these black and white laws backed up by punishment, there are various loopholes you can find that satisfy the letter of the law but are still plenty "indecent" to the conservative folks who don't like it. A voluntary decentralized mechanism allows them to fully express their judgment, and generally makes it easier to establish communities with people who agree with them.