Cross-dressing, Men's Garments, and Women's Garments

"No, thanks. I'm very cold. Could I borrow your jacket?"

"It's a man's jacket," he said, hesitating.

"I'm very cold, David."

"You're not-" He broke off and slipped the jacket from his thin body and draped it over my shoulders. "Let me carry that for you," he said, and took the Times from under my arm.

(Page 214, Davita's Harp by Chaim Potok)

*

This is one of the most beautiful moments I can recall in Jewish literature.

David believes it is a sin to allow Ilana to wear his jacket, however, due to the circumstances (she has just found out her father may have died in a bombing, and is suffering from shock) he realizes that he can put aside his stringencies and allow her to wear his jacket.

The question is- is this truly a sin?

Let us look at the verse in Deuteronomy that discusses this, located at Devarim 22:5.

ה לֹא-יִהְיֶה כְלִי-גֶבֶר עַל-אִשָּׁה, וְלֹא-יִלְבַּשׁ גֶּבֶר שִׂמְלַת אִשָּׁה: כִּי תוֹעֲבַת יְהוָה אֱלֹהֶיךָ, כָּל-עֹשֵׂה אֵלֶּה. {פ }

5 A woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment; for whosoever doeth these things is an abomination unto the LORD thy God. {P}

When I read this verse (and this may just be my interest in linguistics and semantics showing through) I notice that a woman is not allowed to wear a "khli gever" whereas a man is told he may not wear a "simlas isha." This seems to denote a difference, where a woman may not wear, as the English translation states, "that which pertaineth unto a man," i.e. anything that belongs to/ has to do with men, whereas men are specifically forbidden to wear the "simlas isha," only the "garment of a woman." It does not use the same terminology, "khli isha."

Why is this? I have looked at the various commentaries, and come up with several thematic answers.

1. Khli ish refers to everything that is associated to/ with a man, namely, his armor, weapons, belt and clothing, as opposed to simply a garment

2. (The most frequent answer) These laws are in effect to prevent neiuf, or adultery/ promiscuity/ immoral behavior.

Now, in Judaic law, do we usually judge according to the letter of the law or the spirit of the law? It seems to me that we have room to be lenient according to the case. In the case of a ba'al sorer umoreh one is extremely strict in that the boy must devour exactly the correct quantities of meat and wine at exactly the correct age in order to have sinned. In the case of an accidental murderer, on the other hand, the intent is what matters more, for the man must flee to an ir miklat, or city of refuge.

Another question- why is it that a woman's garment is a "simlat isha" but a man's article is a "khli gever"? Wouldn't we find it more logical to oppose "ish" and "isha" as opposed to "isha" and "gever"? If the root of "gever" lies in gevurah, this implies that this commandment specifically refers to the warrior, the man of strength, the hero, as opposed to an ordinary "ish."

The next logical place to look is the Talmud. At Nazir 59a we seem to become even more confused. Because while it seems logical that a woman would not be able to wear the accoutrements of war (in R Eliezer b. Jacob's view) why would the shaving of hair be considered the wearing of a "simlas isha?" Also, how can we learn out the prohibition against using cosmetics/ makeup from this? Isn't there a reason that the terminology is different? "Khli" means more than a garment, but how does one make "Simlas" into cosmetics or bodily hair?

I came across an interesting paragraph here:

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. As the Tur (c. 1300 C.E.), the predecessor code of the Shulhan Arukh, puts it: "A woman should not dress in clothes specifically for men lefi minhag hamaqom according to the local fashion" (YD 182)."

While all of this is interesting and informative, is there an actual statement/ law/ ruling? Is an item forbidden because a man had it in his posession (i.e. owned the jacket before someone else, even if it is unisex) because it is actually made for a man (i.e. a man's jacket only) or does this only refer to the specific accoutrements of the "gever," the warrior? And as to the "isha," how does her simlah relate to cosmetics and her adornments?

That's what I've been wondering lately.