This is a superb, must-read post. I will disagree with one point, however, which is not central to the thesis of the article but still very relevant.
"The gender benders of the 1980s were doing something genuinely radical. They demonstrated that biological sex and gender presentation could be separated without requiring a claim about inner identity. Boy George did not claim to be a woman. Annie Lennox did not claim to be a man. The affirmative model collapses precisely this distinction, insisting that cross-sex presentation is evidence of cross-sex identity and that discomfort with gender norms is evidence of gender incongruence. The gender benders suggested something different and developmentally more liberating. They suggested that the norms themselves were the problem, not the person failing to fit them."
The distinction being described here, even if possible in theory, seems to me very hard if not impossible to maintain in practice. I don't think it's an accident that Judith Butler, who helped lay the theoretical foundations for the erasure of sex, gained prominence in the context of 1980s gender bending culture. At some point, radical gender bending is bound to invite speculation followed by forthright criticism of the very idea that humans are sexually dimorphic and that sex is defined by the organization of the body toward production of one of two distinct gamete types. (Trans, in the contemporary sense, is the theoretically incongruent marriage of this idea to that of "gender identity," which evolves out of 1960s psychology.)
That's not to suggest that deviation from traditional sex roles is bad or should be condemned. It can, of course, be liberating and, up to a point, good. And it must be tolerated in a society that values free expression. But the notion that a clear, bright line can be drawn and--crucially--enforced between David Bowie-like gender bending and what we've come to know as gender ideology is one I find unconvincing. The attitudes and institutions that permit the one will, with time, almost certainly compel the other.