Every Halloween, amidst the sea of short skirts, boobs and 90s kids-show characters, I always seem to notice a few costumes that make me pause and wonder “Um, is that okay?” I’m not talking about costumes with those bustiers that cause more pudge to spill out than should be allowed, or those God-awful Borat thongs that have caused me to see more butt cheeks than I’ve ever wanted to. I’m talking about the ones that tiptoe that fine line between “Meh, kind of funny” and “Wow, that’s racist.”

Maybe I’m overly sensitive to the idea of racial stereotyping because of my days spent at the University of Illinois, where our mascot was a Native-American chief, and ghetto-themed Greek parties seemed to crop up every other weekend. But something just rubbed me the wrong way when I was browsing the Internet for Halloween costumes and stumbled upon the Wild West themed section, a menagerie of Native American and Mexican-based costumes, like the “Dream Catcher,” the “Pocahottie,” and the “Sexy Bandita,” complete with tequila-bottle holsters! Sluttiness of the costumes aside (that whole dressing as a sexy fill-in-the-blank trend is a completely different issue), I was dumbfounded. How, in 2010, do we have costumes like these for sale? But these are not even so bad compared to some of the homemade costumes I’ve seen while out celebrating. Longing for the days of minstrel shows? Why, just head out to Clark Street this weekend, and you’re bound to run into a painted blackface or two!

But like I said, these costumes walk a very fine line between okay and not okay, and I have trouble deciphering what the key element is that makes it wrong. Except for the instance of blackface, which is never right. But why is it that I think it’d be okay, and actually kind of funny, for someone like me who owns more cardigans than Mr. Rogers, to dress up as a chola for Halloween, but would be a little put off by a blond-haired, blue eyed girl doing the same thing? I was raised a studious little nerd in the suburbs. I probably have no more ties to that counter-culture than this fictitious blondie does, aside from brown skin and a tilda in my last name. So why is it okay that I poke fun at something that’s probably just as far removed from me than it is for her?

If my Caucasian husband came home from one of those pop-up Halloween shops tonight with a Pancho Villa costume, I would not be offended in any way. Considering his affinity for Hijos de Villa tequila and a hilarious story about the first time he drank said tequila, I would most likely commend him for a nice costume choice. But would you think it was as funny if you saw him at the bar? I know if I saw a guy who wasn’t Mexican sauntering down the street in a sombrero, fake mustache and serape, and I had a little bit of Hijos de Villa in me, I’d probably ask what his problem was. Is it personal history that makes a costume choice acceptable? Or should we just accept that Halloween is an offensive holiday, whether it be sexually, racially or just tasteless in general?

I don’t know that I really know the answer. And I don’t know that what I consider to be non-offensive is truly okay. I just know that this weekend, for every 5 Snookies, Sookies and Gagas, there will be a least one costume that makes me question that person’s racial sensitivity. Perhaps before we all head out, we should take a look in the mirror and ask ourselves, “Does this make me look racist?”

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