Only a few sources spell out what is meant by “women’s clothing” and “men’s clothing.” Women normally wear colorful clothes; men wear white.Most sources leave the particulars undefined, because they realized that while gender distinction in dress is almost universal, the particulars are a matter of local fashion trends. The intent of the law, in this view, is to prevent men and women from associating with what would normally be a single-sex group of the other gender under false pretenses for purposes of, or in circumstances that are liable to lead to, heterosexual adultery. Thus men and women cross-dressing in other circumstances might not be prohibited, at least if it can be assured that the “abhorrence” will not result.Nonetheless, some of our sages read these two clauses as if they were the statement of two identical rules, one applying to men, one applying to women.That is, they read it as if it says, “a man or a woman shall not wear the items of the other gender.” But most sages treat the two verses as distinct in intent.In societies in which gender segregation was widely observed, this subterfuge was seen as a real danger.This was even before the production of “Yentl.” It is stated this way in Sefer Ha Hinukh: “The root of this mitzva (commandment) is to keep us from sexual sin…and there is no doubt that if men and women’s clothing were the same, they would mix and the earth would be filled with impropriety” ( 564).Given the context, there is no danger that such cross-dressing will lead to heterosexual adultery.The danger of “cross-dressing,” according to the analysis followed here by and the Shulhan Arukh, is that it might allow men to enter women’s groups and women to enter men’s groups.
A common understanding of our verse in exegetical and halakhic literature is stated by is defining the reason for the law or, alternatively, its scope.It would have been “unlady-like” for her to use a sword — worse, a violation of the law — because a sword is a man’s tool and so the righteous woman of valor finds an alternate weapon.While this interpretation does not prevail in later halakhic discussion, it does appear, and so it must be regarded as a viable albeit minority view as to the intent of the first clause.Moreover, none of the mainstream halakhic (legal) interpretations of this verse follow the midrash of Pseudo-Yonatan.Thus, this interpretation, while interesting, has no legal weight.Any miscue is considered either funny or offensive, any crossover at best avant garde and at worst degenerative or subversive.Many viewers of films such as “The Crying Game” and “The Birdcage” see crossdressers as either laughable or pathetic, or both.If the Torah had wanted to prohibit men from going out among women in women’s dress it could have said that.This context of social mixing of men and women is imposed on the verse.Generally speaking, gender clues have been incorporated into clothing style, even for infants, in order to prevent misidentification.And so it would seem at first glance that our Torah holds such a concern, as our verse from Deuteronomy seems to prohibit “crossdressing.” Let’s look at the passage and how it has been interpreted by our sages. (1) A man’s item shall not be on a woman; (2) and a man shall not wear a woman’s garment; (3) whoever does such a thing is an abhorrence unto Adonai.