Looking at Deuteronomy 22:5–The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the LORD thy God. ... Is not abominable to God under the new convenent? Thank you 🙂
***This law is one of the 500 some-odd laws that Jesus condensed into his first and second great commandments. There is a strong belief that Jesus inferred that we need only focus on his two commandments, rather than on the 500 some-odd laws. More to the point, perhaps, James 2:10 says “…whoever keeps the whole law [of the Old testament] but fails in one point has become guilty of all of it.” So, it is easier to abide by Jesus’ two commandments.
That said, one may not necessarily have to fear being struck by lightning if one wore garb of the opposite sex, under certain circumstances. One may be acting in a play, for instance, or one in the follies of sexual encounters may look to impress their lover in some kinky fashion, yet one who does so would not actually think of themselves as a member of the opposite sex inside.
A variation of this is when Jesus addresses the issue of being kosher. He says in
Matthew 15:11, “it is not what goes into the mouth that defiles a person, but what comes out of the mouth; this defiles a person.” In the same sense, a person can wear whatever they want, so long as they love God in accordance with the second commandment of Jesus. To that extent, though, as God abhors those who act as if they were of another gender in terms of the people they are intimate with, people of one gender should not believe or desire to be another gender, regardless of what they wear.