All the strict dress codes for women, and bans on women's slacks, sure worked good for Josh Duggar, didn't they?
At the time that the command of Deuteronomy 22:5 was given, I do not believe anyone in or around Palestine wore any kind of slacks or pants. Everyone, men and women, wore robe-like garments. So just what was Moses talking about, when he said a women must not wear a man's garment? (And why does that command not apply to the wearing by women of T-shirts, jackets, baseball caps, tennis shoes and tube socks, all of which are worn by men?) I don't pretend to have the final, definitive answer as to what Moses was talking about. However, it is interesting to note Josephus' commentary on this passage: "Take care, especially in your battles, that no woman use the habit of a man, nor man the garment of a woman." [Antiquities of the Jews, Book 4, Chapter 8:43]. Could this have been intended as a prohibition on women in combat?
Also, the passage appears in a section which begins with this statement in Deuteronomy 12:1 - "These are the statutes and judgments, which ye shall observe to do in the land, which the Lord God of thy fathers giveth to possess it, all the days that ye live upon the earth." These commands apply to the ancient Israelites while they were living in the land of Israel. We don't normally obey these commands today, such as the "Everybody Must Get Stoned" command to kill proponents of false religions by stoning, Deuteronomy 13:8-10, or the prohibition on mutilated men joining a church, Deuteronomy 23:1.
If you think I am a compromiser for saying these things - well, you might be an IFB.