In today's Baltimore Sun, I am quoted saying that "Halloween costumes are an excellent measure of who it's still okay to hate or belittle." Let's explore:
Due largely to the civil rights movement, Black Americans have managed to politicize their representation. It is now largely unacceptable (in most circles) to dress up as a Black person for Halloween. However, you will see people dressed up as "Indians" every year. These caricatures, anachronistic as they are, suggest that American Indians no longer exist. Of course, they do (and they are as "modern" as the rest of us), and they have to watch their history and, often, their religion parodied and caricatured every Halloween (and at sports events, still).
Similarly, it is still perfectly fine to dress up as a "redneck." Rural working class people in this country are real people who deserve respect and dignity, but we don't have a strong class movement in the U.S. and so it remains rather acceptable to be overtly hateful towards or dismissive of the poor, especially the white poor, since poor people of color have some protection because of the politicization of race.
Women are a striking case because feminists have tried incredibly hard to politicize the representation of women and failed. A glance at any magazine stand will demonstrate as much. The popularity of dressing up as a sexy demonstrates that women and girls use Halloween as an excuse to emphasize their femininity, to be purely female, an object on display, something to be drooled over and desired (see some examples here).
One sexy costume available this year is the Anna Rexia costume. This costume reveals the paradox that young women live with, and often embody. Women are told that being thin makes them powerful. And many of us, whether we like it or not, admire very thin women and wish that we could get our bodies like theirs. They are, indeed, achieving an ideal and this is why we envy them. But they are achieving an ideal that is also belittled. In many ways, being feminine is the same thing as being powerless (being submissive, passive, not too loud, not having strong opinions or desires) and being thin is a way to be insignificant (to be less than, to not take up too much space, to be overlookable). So women who perfect their own femininity, sometimes through anorexia, are attaining a perfection that undermines instead of undergirds their power. The Anna Rexia costume reveals that we have contempt and disdain for perfect femininity. Being a perfectly feminine person is kind of like being a perfect idiot.
Perhaps the ultimate evidence that femininity is hilarious or ridiculous, or even frightening or disgusting, is the fact that men use the category "woman" as a costume. They are not doing so to revere them, they do so to mock them. And it's not simply about being something you're not. You very rarely see women dressing up like men. Masculinity simply doesn't get denigrated as funny or stupid.
So, ultimately, one of the most disturbing parts of Halloween, for me, is the combination of men who are mocking femininity and women who are emphasizing it. That is, while men often go around dressed like women (teetering around uncomfortably in high heels with garish make-up and grotesque fake boobs), women are teetering around uncomfortably in high heels with garish make-up and (grotesque) (fake) boobs. The irony, apparently, is lost on everyone.