The story is told of a pentecostal group that almost split over a teen ice skating party. The problem was Deuternomy 22:5 and its interpretation:
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.
One part of the church insisted that the girls wear skirts. Another part was horrified as the teen boys might get a glimpse of forbidden territory if a girl fell. But pants, the other group said, pertaineth to a man and should not be worn! Eventually a compromise was reached—the girls would wear pants under their skirts!
The Easton Dictionary has this to say on clothes in its article on Dress:
The robes of men and women were not very much different in form from each other.
This leads me to think that something other than transvestitism is the issue.
The Hebrew word here for man is not the standard word—adam. Instead The Enhanced Strong's Dictionary tells us it is this word:
h1397. גֶבֶר geber; from 1396; properly, a valiant man or warrior; generally, a person simply: — every one, man, x mighty.
AV (68)- man 64, mighty 2, man child 1, every one 1;
man, strong man, warrior ( emphasising strength or ability to fight)
While the word can and does mean man, it also can and does mean warrior. Here is what the Theological Wordbook of the Old Testament tells us about geber:
גֶבֶר. Man. As distinct from such more general words for man as אָדָם, אִשׁ, אֱנוֹשׁ, etc., this word specifically, relates to a male at the height of his powers. As such it depicts humanity at its most competent and capable level. Sixty- six occurrences.
The word is related to warrior, and is often used of men who, based on the context of the word in the sentence and passage were warriors.
So how then could Deuteronomy be translated?
5 The woman shall not wear that which pertaineth unto a warrior, neither shall a warrior put on a woman's garment: for all that do so are abomination unto the Lord thy God.
Historically there are examples of this. Pisistratus in ancient Athens is a good example. He wanted to gain control of Athens and start a war. So he found a tall distinctive peasant woman from the provinces and dressed her up as the Goddess of War and Wisdom, Athena, and announced to the people that the Goddess was in favor of the war. He got his war.
Another example is the Urgaritic legend of what is called the Daniel Cycle. This is a series of stories about an ancient stereotypical wiseman. He was mentioned in Ezekiel 14:14. One of these stories was that Daniel was insulted and his son refused to avenge his father. This was a scandal. It was so shocking that Daniel's daughter dressed up in armor and avenged her father. A shocking reversal of roles.
The idea is that one magically imbues the woman with warrior power. "Our women are better warriors than your men." The same thing occurs when a warrior is feminized. "Your men are like women to us."
This latter idea may be what was going on with the angels and Sodom. The idea was to show the superiority of Sodom by using the visitors as if they were women. "We make your men our women." Remember that the men of Sodom after the gang rape would have gone home to their wives. Homosexual rape in military situations is a lot more common than people think. I have seen estimates that 1/3 of all rapes are homosexual in nature, many of them are never reported.
Historically, the rape of males was more widely recognized in ancient times. Several of the legends in Greek mythology involved abductions and sexual assaults of males by other males or gods. The rape of a defeated male enemy was considered the special right of the victorious soldier in some societies and was a signal of the totality of the defeat. There was a widespread belief that a male who was sexually penetrated, even if it was by forced sexual assault, thus "lost his manhood," and could no longer be a warrior or ruler. Gang rape of a male was considered an ultimate form of punishment and, as such, was known to the Romans as punishment for adultery and the Persians and Iranians as punishment for violation of the sanctity of the harem. Donaldson, Donald. (1990). "Rape of Males," in Dynes, Wayne, ed. Encyclopedia of Homosexuality. New York: Garland Publications.
The point to remember is that the differences in clothing among men and women were minor, so it seems likely that something else besides gender distinctions is in mind in Deuteronomy. The use and respect for magic and the power it was supposed to have is a theme of the Old Testament that we moderns do not fully appreciate.
I would paraphrase the passage this way:
5 Do not dress a woman as a warrior, or a warrior as a woman for pagan magical practices: for all that do so are an abomination unto the Lord thy God.
The issue of gender-suitable clothing is a cultural issue. A Scots man dressed in a kilt is not the least bit effeminate. Deuteronomy 22 does not seem to be addressing this issue.