Women in Kilts?

[Nanook]

At the end when she reveals her true gender she gets the "not wearing that which appertaineth to a man" bit. This quote has been bandied around in many contexts (and usually without reference to the original one) and still exists in the unconcious mind of some.

The Halacha (or commandents) is question is the prohibition of not wearing gender specific clothing of the corresponding type.

“A man’s clothes should not be on a woman, and a man should not wear the apparel of a woman; for anyone who does these things, it is an abomination before G-d.”

לא־יִהְיֶה כְלִי־גֶבֶר עַל־אִשָּה וְלא־יִלְבַּשׁ גֶּבֶר שִׂמְלַת אִשָּה כִּי תועֲבַת ה׳ אֱלהֶיךָ
כָּל־עשֵׂה אֵלֶּה

The men's items are not pants but tsitsit and tefillin. Yentl was clearly guilty on all counts.

The question is why? There is a relatively large literature on this passage. The general consensus of commentary is that the prohibition is about the will to deception (Yentl again) to commit sin (the sparing moment for Yentl). Rashi, for example, saw the deception as the will to adultery (" this is only for the purpose of adultery." and "So he can go and be among the women.").

Alone the observation that someone might suggest that a man in kilt is a man in a skirt is an exclusion to this prohibition since it is hardly a deception. A big hairy guy with a beard is a dress (such as a late "Coco Vega" who was a fixture of the late 1970s and early 1980s San Francisco party scene) might look like a wack but hardly a gender deceiver. It only crosses the line when there is an intent (conscious will or desire) to misrepresent gender to violate other laws.

What is "gender specific" is defined by local custom. Its application among Charedi (conservative Orthodox in contrast to "Modern Orthodox" Jews) is to forbid women from wearing pants or only (under specific conditions) under a skirt that is clearly identifiable as and accepted in the local area as a women's skirt.