“A woman shall not wear a man’s garment, nor shall a man put on a woman’s cloak, for whoever does these things is an abomination to the Lord your God.” -The Lord God of Heaven
I have heard it said that this doesn’t mean women shouldn’t wear pants because at some other point in history men wore dresses and women wore something like pants. This is like saying that if the meaning of a word has changed it might as well have no meaning. So feel free to use the N-word liberally. Also use the word gay to mean happy or whatever you want. Jesus and his disciples also wore thongs. This is silly. In our culture dresses are clearly associated with women. Except of course, as Chesterton says, when men want to rule. That is priests, judges, etc wear dresses as a sign of authority and respect. We even recognize this which is why we wouldn’t like it if our pastor wore a robe, we love the casual. But the fact remains that pants were developed as technology enabled them to be girded clothing, for work, for function. In our cultural language dresses are clearly associated with women, and pants with men. Long hair is clearly associated with women and short with men. So why wouldn’t you want to be as careful as you could? God says it is an abomination. Make the lines as clear as you can. As someone raised in the church, I love dresses on women and it saddens me that they are going away. What are we trading them for? Convenience? Our personal comfort? Why not make the very small sacrifice and make God’s created order shine to the World even brighter?
In addition this verse is talking about women putting on war clothes. Obviously apart from the language, this is an argument from the lesser to the greater, if mixing clothes are bad, what about mixing tasks. It is shameful for a woman to go to war, to act like a man. It’s shameful for a man to act effeminate. The language of how we act is just as real as actual language, and God cares about it. And the world notices it even if they wouldn’t admit it.
So just because language can change does not mean it is meaningless. It matters. Just because it is a difficult issue doesn’t mean we just throw up our hands. We are called to be wise, to rightly divide the word of truth. We are to judge the angels. We are supposed to do the hard work of studying the Old Testament rules and Wisdom and apply it to our lives as best we can. Otherwise we are just taking our cues from the world and being lazy.