This is the only verse that addresses the issue of cross-dressing yet there are a wide variety of interpretations as to what it is trying to tell us. The three most common views are:
It is based on some form of connection to Pagan religious ceremonies
It prohibits certain deviant sexual practices that were rampant in Canaan at the time
In some way it was intended to maintain the proper distinction between the sexes.
Here are summaries of each author:
Brown, Raymond - "there are two likely reasons for the uncompromising prohibition. First, there was probably a serious moral issue at stake here. Sexual promiscuity was rife in Canaan, and transvestite practices were part of the corrupt and immoral context of the land... This prohibition is a warning to the Hebrew people not to identify with the degrading sexual...practices of the Canaanites. ...Secondly, it is also likely that there were religious reasons for this regulation. Some pagan religions ...demanded that men and women exchange their clothing as part of their fertility rites."
Bruce, F.F. - "Within living memory, this verse has been cited against the wearing of trousers by women; yet there has been no corresponding refusal to wear rayon/cotton or terylene/worsted mixtures. The practice referred to may have been thought to have magical effects. There is certainly evidence of transvestism and simulated sexual inversion being associated in the ancient world with sexual license -- and in a religious context."
Clarke, Adam - "It certainly cannot mean a simple change in dress, whereby men might pass for women, and vice versa. This would have been impossible in those countries where the dress of the sexes had but little to distinguish it, and where every man wore a long beard."
Daily Bible Commentary - "Verse 5 arises out of the scriptural concern to guard the built-in distinctions of God's creation. It does not specify particular forms of dress for the two sexes; these will legitimately vary with time and place. What is condemned is the perverted misuse of current custom; and since this is 'an abomination to the Lord' we are to regard this law as permanent, and respect its wisdom."
Elwell - "Transvestism is prohibited because of its association with homosexual practices or the cults of certain deities, or in other cases possibly because of its use in magical practices to cure infertility."
Expositor's Bible Commentary - "The prohibition against a woman wearing the habiliments of a man and of a man wearing the clothing of a woman can scarcely refer to transvestism. Though evidence for religious transvestism in ancient Canaanite religion is not conclusive, the inclusion of this rule under the proscription of the things the Lord detests suggests a serious problem, one that involves alienation from the Lord because of the adoption of the proscribed religious practices. Most probably illicit sexual practices...are included in this prohibition."
Freeman, James M. - Explains that pagan religions frequently worshipped idols depicting the features of one sex and the clothing of the opposite sex. Worshippers often cross-dressed to participate in religious rituals. So, one interpretation is to avoid cross-dressing because it was part of idol worship....
Gray, James M. - Doesn't mention the verse, but he does caution against concentrating on small portions of the Bible to draw conclusions. He encourages serious students to study multiple chapters in order to obtain a comprehensive knowledge, and to place individual verses in their proper perspective.
Hamilton, Victor P. - "There are three possibilities here. One possibility is to view verses 1-12 as a collection of heterogeneous laws. A second approach is to attempt to relate some of the laws at least to each other by a common word or theme... A third...is that [it] deals with procedures of wartime."
Henry, Matthew - "The distinction of sexes by the apparel is to be maintained, for the preservation of our own and our neighbor's chastity. Some think it refers to the idolatrous custom of the Gentiles: in the worship of Venus, women appeared in armor, and men in women's clothes. It forbids the confusing of the dispositions and affairs of the sexes. Probably this exchange of garments had been used to gain opportunity of committing uncleanness, and is therefore forbidden."
Interpreter's Bible - "A law appearing only here and usually interpreted as directed against the simulated changes of sex in Canaanite religion... It may be that the motivation comes from the Israelite abhorrence of all that is unnatural, though in point of fact we have no certainty as to what lay behind it."
Jamieson, Fausset, Brown - "Though disguises were assumed at certain times in heathen temples, it is probable that a reference was made to unbecoming levities practiced in common life. They were properly forbidden; for the adoption of the habiliments of the one sex by the other is an outrage on decency, obliterates the distinctions of nature by fostering softness and effeminacy in the man, impudence and boldness in the woman as well as levity and hypocrisy in both; and, in short, it opens the door to an influx of so many evils that all who wear the dress of another sex are pronounced, 'an abomination unto the Lord.'"
Lamsa, George M. - Points out that in the Eastern culture, women were generally respected, and not searched or molested. They were allowed to travel relatively freely. Men dressed as women might be able to smuggle contraband or spy on their enemies.
MacArthur Study Bible - "Found only here in the Pentateuch, this statute prohibited a man from wearing any item of feminine clothing or ornamentation, or a woman from wearing any item of masculine clothing or ornamentation.... This instance specifically outlawed transvestism. The creation ordered distinctions between male and female were to be maintained without exception."
Maxwell - "One explanation is that this practice was associated with the religion of Canaan... Apparently women appeared in male garments and men in women's clothes when they worshipped pagan deities. Yahweh wanted His people to be unique and do nothing that was in any way connected with foreign religions. Another theory is that this verse could refer to war. A woman was not to put on the trappings of a soldier or dress like a man in order to gain admission into the army..." Another explanation...is that it obscured the distinction between the sexes and therefore violated an essential part of the created order of life... During the days of Moses, garments worn by men and women were very similar so this command was designed to keep a woman from appearing as a man for purposes of licentiousness... This passage teaches against the wearing of any item specifically intended for the opposite sex... Still another...refers to the practice of transvestism, a deviant form of sexual behavior which is often characterized by cross-dressing...and in the ancient world its practice was associated with the cults of certain deities."
McGee, J. Vernon - "Someone will say this does not apply to us today because we are not under the Law. That is true. However, all these laws which we are studying do lay down certain principles which we do well to notice. I may be out of step with the times, but I believe it is still true today that a woman looks better dressed as a woman, and a man looks better dressed as a man."
Merrill - "a regulation that seems most intrusive in the overall passage. Kaufman offers the suggestion that the theme of separation...finds parallel in the separation between a mother bird and its young in the next law. Inasmuch as the latter at least indirectly touches on the subject of death...the law of transvestism may also do so by association."
Payne - "There is good reason to suppose that the law of verse 5 is not concerned with the mild sexual aberration known as transvestism, but is a repudiation of certain pagan religious practices of that era; so this law is no more a fashion guide for today than is the law about tassels in verse 12."
Peake - "5 is one of a series continuing in 9-11 whereby mixture of garments, seed, animals and materials are prohibited. They are obviously ancient laws, the neglect of which brought religious risk of some kind, for a mixed crop became holy or forfeited to the sanctuary."
Plaut - "The Torah forbids the wearing of apparel customary for the opposite sex. From this rule, tradition concluded that men's apparel included implements of war, and...a woman was not supposed to wield a man's weapon... This also meant that women were precluded from joining the army...the rule further implied that women were forbidden the wearing of talit and tefillin (prayer shawl and phylacteries).... priests of Hercules dressed as women; while, in Rome, men who participated in the vernal mysteries of that god did likewise. So too in the cult of Dionysus, males often adopted feminine costume, just as at the annual festival of Oschophoris... The same practice is attested also in connection with the cult of Leukipposin Crete... According to some scholars, it is a method of assimilating the worshiper to the person of the deity...to others, it is a form of disguise, designed to foil demons and other noxious spirits. Probably...there was no single origin for all the examples of this practice... It has also been suggested that, in cases where men wear women's clothes in the performance of magical rites, this reflects the widespread belief that magic (especially when it aims at promoting fertility) is primarily the province of the female."
Richards, Lawrence O. - Doesn't mention the verse.
Schocken Bible - "This prohibition touches on a frequent theme in Leviticus: the improper mixing of categories."
Schultz - Doesn't mention the verse.
Thompson (J.A.) - "this law in its original setting has no direct implication for modern life."
Tilsen, Rabbi - "The Torah's concern in this verse, then, is not with creating or reinforcing gender differences per se, but in preventing gender associations of clothing or possibly body hair from being used to deceive others for purposes leading to sexual immorality. The key here seems to be deception for illicit purposes. Indeed this law appears in Deuteronomy in the context of laws against deceit...While the legal interpretations of this verse from Deuteronomy have been diverse, most of Jewish legal discussion has not taken the verse to suggest a blanket ban or condemnation of what today we call cross-dressing."
Walvoord, Zuck - "The adoption of clothing of the opposite sex was forbidden because it obscured the distinction of the sexes and thus violated an essential part of the created order of life. It was also perhaps associated with or promoted homosexuality... Also some evidence exists that transvestism may have been connected with the worship of pagan deities."
Wenham, Motyer, Carson, France - "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... It is possible too that some rituals of non-Israelite religions involved transvestism, and that practice is condemned for this reason."
Wesley, John - "This is forbidden, both for decency sake, that men might not confound those sexes which God has distinguished; that all appearances of evil might be avoided, such change of garments carrying or manifest sign of effeminence in the man, of arrogance in the woman, of lightness and petulance in both; and to cut off all suspicions and occasions of evil, which this practice opens a wide door to."
Zondervan - "The prohibition against a woman wearing men's clothing and vice versa can scarcely refer to transvestism. Most probably illicit sexual practices..."
Which view is correct?
Can anyone be certain they know the mind of God?
Are the rest of us speaking for the Devil?
Is this insistence on automatic sin a stubborn adherence to dogma?
Is it simple ignorance?
Is it personal arrogance?
What do you think?