1. Use your imagination.
Halloween is awesome because it's a holiday of all the the stuff that floods our imagination. The paranormal, the fantastical, even drawing on history can be a super dope way to come up with ideas for a costume. If imagination isn't your thing, you're going to continue to get more and more uncomfortable at these Halloween gatherings now that we're gaining momentum here in the era of the mainstream nerd. Imagination is our greatest and most under-utilized gift. If you have a shortlist of mexican drunk, indian, and oriental dragon lady, you're in trouble; and in more ways than one. Google super heroes, dig through your movie collection, or maybe (and this could be a stretch) you've read a book recently you could draw inspiration from? Hell, make up a character and their back story. Who says it needs to be instantly recognizable? Also, a unique costume is a great conversation starter, and reveals things about you to say...other potentially interested parties.
2. Recognize the difference between a character and a caricature.
...or a type of fictional archetype, as opposed to representing people who actually exist in our world... Wanna be a troll? Tight. Gandalf? Awesome. Gandalf and trolls are both fictional conjurings of the imagination. For example, "Indians" are not the fictional, stereotyped images you see in popular culture and it is not at all awesome to slap on some stupid hippy outfit while brandishing a fake hatchet like you just dropped out of some ridiculous western movie. We are not living in the 1950's where it's cool or acceptable to play "cowboys and indians". People played that game in real life, and it was ugly. It's an especially brutal history, not a stupid John Wayne film. People died, and it was not the way it looked on practically any film you've ever seen. People of the Indigenous Tribes of the America's, or First Nation peoples, or Native American (Or Ojibwa, Dakota, Inuit, or any of well over 500 nations), are real people; living, learning and working all over the world, today. Right now. Remember this example when you think about why you have the impressions you have of certain cultures, and how different people are than how they're portrayed in popular media. If you don't find yourself thinking about why you have the impressions you have about people of color, now is as good of a time to start as any.
3. Take some time to think about where your ideas of people of color come from.
Seriously. Take as long as you need. Also, consider this:
4. Read a damn book
Look. Intelligence is hot. The more you know, the more out of place you might feel in some ridiculous club where people feel like it's ok to put their hands on others, when it never is (do we seriously still need to say that?)... The plus side is that you'll feel right at home in rooms full of beautiful, smart, and charming muhfuckaz who really know the finer things in life and know how to have a good time without oafing around a room like actual real life trolls straight outta Lord of The Rings. Also, the more you learn, the more you know how to dress up for Halloween without being an asshole.
5. Think your costume might be inappropriate? It's probably not cool. So don't wear it.
Ask yourself, "Would I wear this to the Halloween work party or the Halloween edition of my family reunion?" "Would I want to be on TV wearing this costume?" Would I feel less than entirely comfortable wearing this costume at a party who's friendly party-goers are comprised exclusively of people of color?" If the answer to one or more of these questions is no, I feel pretty confident in advising you to rethink it, homies.
6. Understand that what you intend does not dictate the impact it has on the people, or world around you.
Maybe you're dressing up "as a Mexican" because you're a bigoted ass, but maybe you're a really good person who who thinks Mexicans are funny people that you enjoy laughing with at work. You know, someone who just doesn't get why this is so fucked up. If you're in the latter category, it doesn't mean you should continue with your plan; you don't get a pass. Contrary to the content of the greatest single song of this century, wherein the wise LL Cool J and his enlightened friend Brad Paisley so eloquently elucidate on the idea of "accidental racism", this is not a cute, forgettable offense. Racism is still racism, even when you don't mean it. And you will be called out, and you'd be wise to listen. After all, who can better spot racism than the folks who experience it's salty glare, sour words, and aggressive, micro-aggressive or passive aggressive nastiness on a daily basis?
7. Do not "go as" a member of any race, socioeconomic status, or social identity because that, in itself, is a stereotype, and if you're comfortable with this, you're more than kind of an asshole.
"Going as" a person of a targeted social identity is inherently bigoted and totally within the bounds of getting you called out, uncomfortably gawked at, or slapped anywhere you go in public. (btw, here's the definition of a targeted social identity: Members of social identity groups who are discriminated against, marginalized, disenfranchised, oppressed, exploited by an oppressor and oppressor's system of institutions without identity apart from the target group, and compartmentalized in defined roles.)
You've been warned.
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