Objection: Deuteronomy 22:5

"A woman shall not wear man's clothing, nor shall a man put on a woman's clothing; for whoever does these things is an abomination to the LORD your God. (NASB)

Torah and Christians

Most Christians are well aware, and rightly so, that we are not bound by the specifications of Torah (Genesis - Deuteronomy or "the Law"). Even those who condemn cross dressing for other reasons agree.

While some Christians see Deuteronomy 22:5 as a clear reference to the divine condemnation of transsexuality, most commentators suggest that this passage contains minimal relevance to the debate at all, or indeed to twentieth-century society. It is likely that, in keeping with God's covenantal concern to preserve the holiness of Israel, and to avoid anything which threatened Israel's existence and harmony, the cross-dressing prohibition was introduced to prevent involvement on the part of Israelites in contemporary Canaanite religious rituals of the day which involved swapping of sex roles and cross-dressing. Whatever the significance of this particular verse, it is probably doing a disservice to reasonable hermeneutics to apply it directly to transsexuals. (Transsexuality A Report by the Evangelical Alliance Policy Commission)

True, about the only direct reference you will find on cross-dressing is in Deuteronomy buried in the Judaic code. If we use that verse for a reference we are on shaky ground because most of us do things like eat pork, which is also in there. Besides, the blood of Jesus has set us free from the law to follow a higher law of grace. (Cross-dressing & Christianity by Randall Wayne)

Most pro-trans and pro-binary people will say, "That's Torah, so it doesn't apply to us following the Gospel." While that interpretation is fortunate for trans people, I don't like because it avoids the Spirit of the Torah that Jesus appreciated and is perpetually important. With that in mind, let's discover  the spirit of this verse.

Understanding "woman" and "man"

The obvious reaction of trans people (with exception of some of those pesky genderqueer people who insist on being exceptions) will be that they do follow this verse even in its literal interpretation. The transman says "I'm not a woman wearing man's clothes, I'm a man wearing man's clothes." So we have to address what "woman" and "man" mean in the language and culture of the Hebrews.

"Female" and "woman" share one word as do "male" and "man." While all cultures have more than two genders, the Hebrews did not vocalize it with separate words for sex and gender. Conservative Christians have inherited this cultural understanding of sex and gender so they actually interpret it correctly to understand "woman" as a woman who is also female and likewise with "man." We could translate it literally thus:

A person who is both a woman and female  shall not wear man's clothing, nor shall a person who is both a man and male put on a woman's clothing;

Understanding "clothes"

The Torah was revealed to a culture very different from our own and we should take that into account. Not only did they have different ideas about gender variance (manifested as righteous women and eunuchs) but they had different ideas about cisgender women and men. Some Christian subcultures interpret that women who wear pants are dressing like men and men with long hair are presenting as women. It was not long ago that this subculture was America's culture at large. Since mainstream Christians now want to avoid this silly interpretation, they proposed several frameworks by which to interpret this passage deeper and with more nuance.
  1. "Man's item" refers to a sword. Modern Jews used this verse to argue that women should not join Israel's armed forces.
  2. This is a rule of war that prevents male soldiers from disguising themselves as females to hide themselves from their enemy.
  3. In ancient Israel where the sexes were constantly segregated, this prevented one sex from invading the others' space in order to commit adultery. The second half of the chapter is all about intercourse and marriage.
These three are all reasonable and would suffice to neutralize the objection. However, I believe they are wrong. At least, they are not the most important understanding. I defer to a fourth interpretation: Men's and women's clothing are separated for the same reason the Hebrews separated many items. Only four verse later the Torah says not to plant different seeds in the same vineyard. The very next verse separates oxen from donkeys. The verse after that separates wool and linen. Torah is filled with instructions of separation, especially how Israel must be separate from other nations and Levites separate from other tribes. Different scholars have different theories for the motivation of this but they all acknowledge this theme. I myself believe the reason hearkens to the Collective Unconscious, specifically the mind's need to create order from their chaotic world. Eliade's The Sacred and the Profane explains this principle in depth. As Eliade points out, it is not that categories should never mix, but that such mixture is sacred and must be revered because they are the Coincidence of Opposites. If everyone mixed clothing or every ox and donkey were mixed, the Coincidence would become neither sacred nor revered and we end up with our modern culture with a poor sense of the sacred. Cultures can mix genders properly: Adam, the righteous women, and Christ were examples of that.

Other Opinions

Tranvestiticism, Transgenderism, and Deut 22:5 Good history. Pro-transexual, ambiguous otherwise.

Cross Dressing and Deuteronomy 22:5  A rabbi's analysis. Pro-trans

Deut 22:5 A fundamentalist reading applied to whether women may wear pants. Doesn't mention transgenderism, but certainly anti-trans by extension.