http://www.askmoses.com/en/article/235,118/What-does-the-Torah-say-about-cross-dressing.htmlWhat does the Torah say about cross-dressing?
Firstly, let's define "cross-dressing," of which there are two types. There's the silly party stuff that guys and gals occasionally indulge in for fun, like donning a wig or other garment that makes them appear like a woman (or a man). That (for the most part) is inconsequential.
Then there’s the serious stuff, where guys go en femme from sporadically to regularly, and from one private piece of apparel to a full public make-over. Or when women go all macho, dressing in a very manly fashion.
This latter type of cross-dressing, whichever reason motivating it, is not allowed.
G-d understands that some people have a preference for cross-dressing and acknowledges this reality by mentioning this law in the Torah.
In other words, G-d does not consider one evil or immoral for his or her innate sexual nature or desire, just like He doesn't consider one evil or immoral for wanting to eat non-kosher. G-d doesn't say, "Don't get hungry for pork"--G-d says, "Don't eat pork." Likewise with sexuality, He acknowledges that you may have certain innate desires, but tells you to how to react to them.
In the case of cross-dressing G-d says "A man's attire shall not be on a woman, nor may a man wear a woman's garment".1
It is important to note that according to Jewish law, the prohibition of cross-dressing is only violated when one puts on something that is exclusively the domain of the opposite sex.
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