This rule comes from Deuteronomy 22:5, which states “The woman shall not wear what pertains to a man, neither shall a man put on a woman’s garment: for all that do so are abomination to the Lord your God.” The problem with the interpretation by many of this law is that they didn’t take into account that men and women both wore dresses in that day. God warned men through His servants the prophets that He will raise up their skirts and expose the nakedness of the iniquities they committed they thought were not noticed by God. If one took into account what men and women both wore in that day, then perhaps they would think of the meaning.
What this law meant was that women should not play the role of men and men should not play the role of women. This covers things all along the spectrum. This does not include women working, sports, or anything like that. Women made clothes and other materials to sell them, which would qualify as a job. If a man wears a skirt, stockings, and stilettos, then that is wrong. It is a man being effeminate, which is also written in 1st Corinthians 6:9. Sex change operations and taking hormones to change genders are an abomination to the Lord. To those of you who did such things, but say “Can’t God make mistakes?”, implying God put them in the wrong gendered body, it is not God that made the mistake, but you did.