When I went to Africa in 2007, I encountered a woman who had a shirt that I really, really wanted. It was a vintage baseball t-shirt, most definitely from the 1980’s, and looked to be way too large on her. Because I thought it would fit me, I offered to buy it from her and even give her one of my shirts in exchange.
I thought she would take the offer, but before I could even get the words out of my mouth, she refused. Through a translator, I found out why. In that culture (Zimbabwe), and in many others, wearing clothes of the opposite sex is disgraceful.
It’s a concept I honestly hadn’t thought about too much, but one that is discussed in microscopic detail in Deuteronomy 22:5. This section of the Text is known as the “miscellaneous laws,” precisely because commandments like these have no place in the greater context. They just exist, but because they exist, the Jews were obliged to follow them.
But why does God regulate men wearing women’s clothes and vice versa?
Some believe this has to do with blurring the lines between men and women, which could also create a situation where someone interacts romantically with the same sex, creating an inadvertent case of homosexuality.
Others believe it has reference to a deviant type of fetishism, where the sexual appetites extend beyond role play into gender confusion. Still more argue that it’s a simple statement against transvestitism.
All of those could be right, or none of them. The only thing that God Himself tells us is that “these things are an abomination” to Him.
That type of wording is usually reserved for pagan religious rituals, and that is indeed another option. If God has in mind a cultic religious ritual—like other ones that occurred in Mesopotamian circles at this time—then the statement is more about religion than anything else.
I think that limits the real view here, though. Regardless of the cause, what God wants is clear boundary lines between the genders. I believe that forms part of the narrative behind head coverings in 1 Corinthians 11: “Does not even nature teach you…”
If that’s true, then it means that it’s up to culture itself to dictate what is appropriate and what is not. That doesn’t mean it’s “up to interpretation,” though, as much as it means that we should be honest about our fashion choices.