Is Deuteronomy 22:5 relevant for Christians and their lifestyle? If not, why not? If yes, what are the implications?
The passage you refer to reads: "A woman must not wear men's clothing, nor a man wear women's clothing, for the Lord your God detests anyone who does this" (NIV).
Most commentators interpret this legislation in terms of the practice of transvestism among non-lsraelites. It is believed that in Canaanite fertility rites the exchange of dress between men and women somehow contributed to the fertility of the land. The evidence for this type of exchange is practically nonexistent. Yet we know that the goddess Anat is described in one document as acting and dressing like a man.
More clear evidence for ritual transvestism is found in the cult of the Babylonian goddess Ishtar. It was believed that a ritual change of sex occurred by exchanging clothes, and on occasion emasculation may have been practiced.
Among the Hittites we also find rituals in which transvestism was apparently practiced, only among men and for the purpose of removing femininity from the man, restoring his masculinity.
Others find in this biblical legislation a rejection of ritual homosexual practices among pagans.
What I have just described are attempts to identify the cultural background for this biblical legislation. There are disagreements among scholars concerning the specific cultural or religious practice that the biblical writer had in mind. This points once more to the fact that ultimately it is the biblical text itself that has the final word in terms of its meaning.
First, we should observe that the prohibition is carefully phrased: "No woman shall wear an article of man's clothing" (NEB). The Hebrew word translated "clothing" (kali) in the New International Version could include more than what is usually implied by "clothing," and therefore '"article[s] of clothing" may be a better rendering.
The emphasis is on the apparel that distinguishes a man from a woman. The man is not to "put on [a] woman's dress" (NEB). The Hebrew term (simlah, "mantle, wrapper") refers to a square piece of cloth worn as a mantle or wrap. This type of clothing was also worn by men, but the difference, according to the authorities, may have been the finer materials and the vivid colors of the woman's dress and its distinctive embroidery.
Second, the context is formed by a collection of different laws dealing with a variety of human actions, seeming to emphasize respect for other persons and their properties and respect for nature. The unifying topic may well be respect for the social and natural order established by God. There is nothing in the context about pagan ritual practices.
Third, a reason is given for the prohibition: the Lord "detests" a person who does these things. It's here that some find the ritual element. The term "detest/abominate" is used in other places to refer to pagan religious activities that are not acceptable to the Lord. But it is also used to refer to social behavior that is repugnant to the Lord (see Deut. 24:4; 25:16). This seems to be the case in Deuteronomy 22:5.
It appears that the legislation under consideration is not controlled by ancient cultural concerns that are meaningless to us, but is in fact based on a very relevant principle for Christians today: that God is a God of order, and He establishes boundaries within creation to preserve the order instituted by Him.
The distinction between male and female was established at Creation when the human race was defined as "male and female." Anything that alters that distinction is rejected. In the setting of the daily life of the Israelites this would be a rejection of transvestism in pagan rituals. But the principle cannot be limited exclusively to that cultural expression, because it is based on the order of creation.
This certainly impacts our lives today. Every Christian should dress in such a way as to preserve the distinction between the sexes. The details in the implementation of the principle are something that, in our complex society, should be determined by the believer in communion with her or his Lord. Although society defines the way we dress, Christians are to select from what society offers that which is compatible with biblical values.