Laws Concerning Preservation of Life, 1-8

22:1 When you see your neighbor’s ox or sheep going astray, do not ignore it; you must return it without fail to your neighbor. 22:2 If the owner does not live near you or you do not know who the owner is, then you must corral the animal at your house and let it stay with you until the owner looks for it; then you must return it to him. 22:3 You shall do the same to his donkey, his clothes, or anything else your neighbor has lost and you have found; you must not refuse to get involved. 22:4 When you see your neighbor’s donkey or ox fallen along the road, do not ignore it; instead, you must be sure to help him get the animal on its feet again.
22:5 A woman must not wear men’s clothing, nor should a man dress up in women’s clothing, for anyone who does this is offensive to the LORD your God.

The transvestism prohibited here ‘may have been a pagan religious practice or viewed as deviant sexual behavior.’ (Harper’s Bible Commentary)

‘The point here is not simply about fashion, but about certain deviant sexual practices, signified by the wearing of the clothes of the opposite sex. Homosexual practice may lie behind the law (see Lv. 18:22; 20:13). It is possible too that some rituals of non-Israelite religions involved transvestism, and that the practice is condemned for this reason.’ (NBC)

Wright agrees that this is not simply about fashion (even though some modern Christians have used it against women wearing trousers and the like).  ‘Almost certainly it is about the perverted crossing of genders either in orgiastic rites involving transvestitism, or in some form of pagan worship, or both.’

Martin Davie cites Chris Dowd, ‘who looks at the prohibition of cross dressing in Deuteronomy 22:5 and suggests that a distinction needs to be made “between someone who is wearing clothing appropriate to their identity and those who are not.” In his view “trans folk not wearing clothing appropriate to their preferred gender are more likely to be in contravention of this prohibition than those who are.” In addition, he says: “unless we took all the Deuteronomic prohibitions seriously, including prohibitions against tattoos, eating shell fish, banking, poly cotton and Freudian therapy,’ it is difficult to justify using the verse as a prohibition of transgender behaviour even if it is read literally.”‘

According to DeFranza, ‘in addition to the possibility that this law is directed against transgender people transitioning, commentators have suggested it may have been established to guard against heterosexual acts outside marriage made possible by gaining entrance to single-sex spaces through cross-dressing or same-sex activities by pretending to be the “other” sex. Alternatively, like the laws prohibiting the mixing of seeds and fabrics, this could be another reminder of keeping things separate—laws that seem random from our point of view, and even counterproductive at times, but that may have been given to remind the ancient Hebrews at every turn of their call to be separate from all other nations. (It is also helpful to remember that many Christians have cited this verse to prohibit women wearing pants.)’  (Understanding Transgender Identities, p166)

Woods agrees that that this prohibition reflects the ‘blurring of mixtures’ found in Lev 19:19, and that it ‘may have sought to discourage homosexuality, or to prevent transvestite practices found in Canaanite and Mesopotamian worship, as suggested by the word detestable (tô‘ēbâ; cf. Deut 12:31; 18:12; 23:17–18).’

This text is discussed by Carolyn Pressler in the Women’s Bible Commentary:

‘In an earlier day, when women were not allowed on stage, this was one of the scriptural passages invoked to demonstrate the immorality of playacting and actors, which involved men dressing in women’s clothes.’

‘Scholars interpret the underlying rationale of the prohibition differently. Some suggest that wearing the clothes of the opposite gender was part of “pagan” rituals and so was to be avoided by YHWH worshipers. Others envision a military background for the rule; men were not to dress as women in order to avoid military service, nor were women to carry a warrior’s weapons into battle. A third proposal envisions men dressing as women and vice versa in order to gain access to members of the opposite sex for the purpose of seduction. Still others maintain that the drafters of the law found transvestitism inherently repugnant.’

The same author notes that this law occurs in a chapter that deals with the prohibition of admixtures (Deut 22:9-11), suggesting that ‘its rationale has to do with maintaining clear boundaries and categories.’  Further, ‘as evidenced by the unusually strict sexual offense laws found later in this chapter, the Deuteronomic authors had rigid views of gender roles, and much anxiety about the boundary-blurring capacity of sexuality. They may have felt that so-called cross-dressing blurred those gender roles and threatened the created order. For those of us who do not feel that the integrity of creation is fundamentally threatened by women wearing slacks, the primary value of the law may be to illustrate how uncertain the biblical bases of dogmatic ethical pronouncements can be.’

Christina Beardsley writes:

Dressing in the clothes of the opposite gender is forbidden in Deuteronomy 22:5, which is part of a series of regulations that also prohibit the mixing, or blending, of various foods and fibres. Although Jesus challenged this religious obsession with purity, and early Christianity included Gentile (non-Jewish) Christians, who did not observe many of the Old Testament laws, some people would argue that this prescription against cross-dressing still obtains. However, it is important to remember that, prior to transition, the transsexual person is not the gender that they are perceived to be. They are a genetic female with male gender identity or a genetic male with female gender identity. It is distressing for such people to assume the clothes and social behaviour of their birth sex – that, for them, feels like ‘cross-dressing’ – and totally appropriate for them to dress and behave in ways which express their true gender identity.

In any case, a brief review of the history of Western clothing shows that fashion has often blurred these boundaries: trousers, for example, once a staple of the male wardrobe, are worn by the majority of women today, while the development of unisex styles, especially for the young, has become standard.

22:6 If you happen to notice a bird’s nest along the road, whether in a tree or on the ground, and there are chicks or eggs with the mother bird sitting on them, you must not take the mother from the young. 22:7 You must be sure to let the mother go, but you may take the young for yourself. Do this so that it may go well with you and you may have a long life.
22:8 If you build a new house, you must construct a guard rail around your roof to avoid being culpable in the event someone should fall from it.

Illustrations of the Principle of Purity, 9-12

22:9 You must not plant your vineyard with two kinds of seed; otherwise the entire yield, both of the seed you plant and the produce of the vineyard, will be defiled. 22:10 You must not plow with an ox and a donkey harnessed together. 22:11 You must not wear clothing made with wool and linen meshed together. 22:12 You shall make yourselves tassels for the four corners of the clothing you wear.

Purity in the Marriage Relationship, 13-30

22:13 Suppose a man marries a woman, has sexual relations with her, and then rejects her, 22:14 accusing her of impropriety and defaming her reputation by saying, “I married this woman but when I had sexual relations with her I discovered she was not a virgin!” 22:15 Then the father and mother of the young woman must produce the evidence of virginity for the elders of the city at the gate. 22:16 The young woman’s father must say to the elders, “I gave my daughter to this man and he has rejected her. 22:17 Moreover, he has raised accusations of impropriety by saying, ‘I discovered your daughter was not a virgin,’ but this is the evidence of my daughter’s virginity!” The cloth must then be spread out before the city’s elders. 22:18 The elders of that city must then seize the man and punish him. 22:19 They will fine him one hundred shekels of silver and give them to the young woman’s father, for the man who made the accusation ruined the reputation of an Israelite virgin. She will then become his wife and he may never divorce her as long as he lives.
22:20 But if the accusation is true and the young woman was not a virgin, 22:21 the men of her city must bring the young woman to the door of her father’s house and stone her to death, for she has done a disgraceful thing in Israel by behaving like a prostitute while living in her father’s house. In this way you will purge evil from among you.
22:22 If a man is caught having sexual relations with a married woman both the man who had relations with the woman and the woman herself must die; in this way you will purge evil from Israel.
22:23 If a virgin is engaged to a man and another man meets her in the city and has sexual relations with her, 22:24 you must bring the two of them to the gate of that city and stone them to death, the young woman because she did not cry out though in the city and the man because he violated his neighbor’s fiancée; in this way you will purge evil from among you. 22:25 But if the man came across the engaged woman in the field and overpowered her and raped her, then only the rapist must die. 22:26 You must not do anything to the young woman—she has done nothing deserving of death. This case is the same as when someone attacks another person and murders him, 22:27 for the man met her in the field and the engaged woman cried out, but there was no one to rescue her.
22:28 Suppose a man comes across a virgin who is not engaged and overpowers and rapes her and they are discovered. 22:29 The man who has raped her must pay her father fifty shekels of silver and she must become his wife because he has violated her; he may never divorce her as long as he lives.

‘According to written law, a man who raped a woman had to take her as his wife (Deut. 22:28–29); there is no recorded instance, however, of the latter ruling actually being enforced or carried out. When a man from Shechem raped Dinah, the daughter of Jacob, he had to plead (through his father) to be allowed to marry her; her brothers did not seem to think that the law indicated he ought to do so (and indeed they decided the consequence of rape was murder, not marriage; Gen. 34). Likewise, Absalom was not forced to marry Tamar after he raped her (2 Sam. 13; if the law in Deut. 22:28–29 was literally practiced, the change in his feelings for her reported in 2 Sam. 13:15 would have been irrelevant).’ (HarperCollins Bible Dictionary, art. ‘Marriage’)

22:30 (23:1) A man may not marry his father’s former wife and in this way dishonor his father.