Personally, I think the influence of Deuteronomy 22:5. which often taken to condemn crossdresser is overrated as source for society’s stigmatizing crossdressing. Most people disapprove first and then go looking for rationales to support that disapproval. Deut. 22:5 was just a reflection of pre-existing attitudes.

Without getting into the specifics of Deuteronomy 22:5 itself,* whose original ambiguities and subsequent mistranslations have been well discussed (not to mention that Christians who don’t keep kosher are technically engaged in “abombination” as well), I think the disapproval has a lot more to do with societal attitudes toward gender roles. There’s more disapproval in cultures where gender roles are more tightly drawn. And it reflects the historical (and current) lesser status that women have. Consequently, when women transgress gender boundaries, while it definitely has upset people, it was more “acceptable” in the sense that they were aspiring to a more powerful role in society. Whereas MTF crossdresers are giving up the privileges associated with the masculine role. (If crossdressing is so wrong, why does the Catholic church have a number of crossdressing female saints, including Joan of Arc–who was actually convicted of crossdressing rather than heresy.)

The other factor is the widespread public perception of the association of crossdressing with homosexuality. I think that has to do with the fact that manhood is often defined less by what it is than by what it isn’t: not feminine, not gay. When we were boys, we’d tease the weaker boys about being gay long before we had any idea what homosexuality was. Because this association is so strong, people just assume that a man who wants to be feminine must be gay as well.

The other big factor is that crossdressing suggests gender isn’t as clear-cut (just as homosexuality–or even more so, bisexuality–does for sexual orientation), which is quite troubling to people who tend toward a black-and-white worldview. As Shannon said, there’s a lot of people who aren’t comfortable seeing the world in shades of gray. Incidentally, this is true of cultures in general. Non-Western cultures, tend to be (but aren’t always), less absolutist in their worldview. Not surprisingly, transgenders tend to be (but aren’t always) viewed in a more accepting manner.

* OK I couldn’t resist–for what it’s worth might also be pointed out that Deuteronomy 22:5 is found among a lot of other Bibical rules that aren’t followed today, including:

  • Requiring a battlement on the roof of your house to preventing anyone from falling off–Deut. 22:8
  • Prohibiting vineyards from being sown with diverse seeds–Deut. 22:9
  • Prohibiting wearing garments made of more than one fabric–Deut. 22:11
  • Requiring fringe on the four corners of your garments–Deut. 22:12
  • If a man marries and then decides that he hates his wife, he can claim she wasn’t a virgin when they were married. If her father can’t produce the “tokens of her virginity” (bloody sheets), then the woman is to be stoned to death at her father’s doorstep–Deut. 22:13-21
  • If a woman is raped in the city and doesn’t cry out loud enough, the men of the city must stone her to death–Deut. 22:23-24