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When you join the Halloween masquerade, you contribute your own particular vision to creating a topsy-turvy world. Men can be Supermen or have exaggerated female features. Bold women become nuns, and shy women, Amazons. Movie and book characters come to life, animals sing and dance, and inanimate objects talk back.
In the workaday world we spend considerable time and effort striving to dress in a way that’s appropriate. At Halloween, “appropriate” is a meaningless term. Anything goes, and the only fashion problem is how to find a costume that suits your mood or interests. It might be amusing, surprising, clever, provocative, or shocking. There is no political correctness on Halloween.

Whatever costume you choose, it will set the tone for your Halloween revel. Donning Fred Astaire’s dashing top hat and tails will feel quite different than assuming the sinister cape of Count Dracula, even though both share a certain elegance. A transformation occurs. This is why we ask, “What shall I be for Halloween?” not, “What shall I wear?” Underneath, you are always yourself, but exploring other roles is a big part of the fun.

Planning your Halloween costume can be as much fun as wearing it. The key is to allow enough time. That way you’ll be able to consider lots of different possibilities and then figure out how best to produce your favorite. This doesn’t mean blocking out an entire day, or even a few hours of your schedule for costume planning. But you might want to start daydreaming about it on the first of October rather than the 30th. You could even organize a potluck supper with friends for costume brainstorming, or a get-together to actually create them.

Of course, if you just don’t get around to a decision until the last minute, you can do it all at once, fast, by visiting a nearby costume store, sorting through the racks, and paying for your choice. Or you can try a costume rental agency if you live in a large enough community. Even if you don’t want to buy your entire costume, these stores can be useful resources for getting ideas or for buying one or two critical pieces of a costume that you otherwise make yourself.

But plenty of good costumes have been produced at the last minute, and more cheaply, by combining odds and ends from around the house. Maybe you have some clothes or jewelry that you never wear because they’re too dated, or too outrageous, or too ugly. At Halloween, they’re the perfect base around which to build a costume. Or consider some more obvious examples: an apron and chef’s hat, painter’s overalls, maybe your old Eagle Scout uniform (if you haven’t put on too much weight), or the luau shirt you bought in Hawaii with the ukulele you brought back for the kids.

A still more creative, and rewarding, approach is to begin well in advance with a little soul searching. Costumes can be based on what you want to project about yourself, what you want to hide, what you wish you were, or what you fear you are.

If you want a costume based on your dreams and fantasies, ask yourself to complete the sentence “I have always wanted to be….” Then allow yourself to try it. Dreams of a change in occupation can have you appearing as an artist, a firefighter, a chef, a circus performer, a ballerina, and on and on. A freckled blonde can experiment with being a sultry brunette. A short person can build some stilts and try being tall. A starving student can pretend to be a movie star.

You can imitate a person you admire—an actor, a politician, or a movie, TV, or book character—or, through caricature, poke fun at one you hate. Topical costumes offer the chance to make a social statement as you entertain your friends. Bill Clinton (gray hair and hat with presidential seal, a big zipper?) and Monica Lewinsky (blue dress, white stain, dark hair, beret, knee pads) were the choice of many last year. Images of the millennium will undoubtedly inspire many this year.

Try having fun with your fears and neuroses and appear as someone or something that no one could have predicted. Fears about becoming fat or old or ugly can be played out in hilarious, and possibly therapeutic, ways. Are you a pacifist who wants to appear as General Patton? A neat person who wants to experience being a slob? A logical person who wonders about gypsy fortune tellers? A feminist who wants to act out her cheerleading fantasy?

Alternatively, if you want to reflect something about what you already are or do, you may want to take your occupation and exaggerate aspects of it in your costume. A nurse, for example, can come as a bedpan, a hypodermic needle, a bottle of pills, or a sleazy Florence Nightingale. A lawyer might dress as a shark, a bank manager as a convict, an at-home mother as an animal trainer.

You might begin with a hobby or interest and express that in a costume. Sports fanatics can come as their favorite players or as sports equipment—a tennis ball, a football, a fish on a fishing pole, a miniature golf course. If you play board games like Monopoly or Scrabble, or play cards, you can make a costume out of them. If you are a couch potato, you can come as one.

You can emphasize some physical characteristic that readily identifies you. If you have a prominent nose, come as one, perhaps carrying a box of Kleenex.

Some people’s favorite costuming tactic is to cross-dress, or reverse roles. Dressing in the costume of the opposite sex has a long and venerable history. Cross-dressing is about gender confusion, power plays, anxiety about the other and about the self. More generally, it is about the confusion of meaning, the impossibility of knowing anything for sure.

Cross-dressing shakes up the most basic premise of our world order, gender identification. It is a practice both fascinating and unsettling, which makes it perfect for Halloween. The approach can be obvious, using exaggerated sexual organs and/or flashy clothes, or very subtle, so that people are confused about whether you are reversing roles or are merely someone who came without a costume.

Of course, you need not come as a person, animal, or thing at all. Consider being an idea or event. A couple we know attended a recent Halloween party as “the parting of the Red Sea.” They had painted a map on their matching tee shirts, and when they stood side by side the outline of the Red Sea was complete. When they separated, it split in two. A new dimension was added at the party when they happened to meet another guest dressed as Moses.

Whatever your costume choice, success lies in the details. Glinda the Good Witch from The Wizard of Oz is that much more fun when she has some fairy dust to throw around. A Shirley Temple costume will become unmistakable if you carry a tape recorder playing “The Good Ship Lollipop” on a loop tape.

To get a costume just right, nothing is more helpful than a little research. If you want to be Elizabeth Taylor in Cleopatra, rent the videotape and study the film. If this sounds too time-consuming, consider the benefits: you don’t have to think of everything yourself. Instead of imagining your costume, you can simply recreate the telling details—the distinctive eye makeup, black pageboy hairdo, and Egyptian-style jewelry, in this case.

For every person or thing (or event or idea), there are certain crucial identifying features, or trademark details, that make the costume. For example, a cow can be any number of different colors, but only an udder, a tail, and horns make it unmistakably a cow. A vampire can wear all sorts of different clothes from elegant to sexy; it’s the fangs, the deathly pallor, and perhaps some dripping “blood” that make you unmistakably a vampire. Add some characteristic behavior—a good “moo” and perhaps the offer of a glass of milk for the cow, “I want to suck your blood” for the vampire—and the masquerade is complete.

In case the perfect costume fails to spring instantly to mind, the pages here contain more than 1,000 suggestions. To help make sense of them, they are organized into categories, accompanied by a list of eight questions to help you if you get stuck.

In future versions, many of the costumes will be illustrated and explained in some detail according to the approach discussed above. The explanations include trademark details and clothing and makeup suggestions, then describe accessories and behaviors to bring the costumes to life. The explanations cover the range of costume making challenges, so that even if the idea you like best isn’t explained, you should be able to figure it out by reading instructions for a similar costume.

In truth, the possibilities for masquerade are endless, and as various as every person’s individual history. New ideas crop up as fast as tomorrow’s headlines, TV schedules, new books and movie listings. Yet for each of us, every year, there seems to be one right choice.

As you approach it, do keep in mind this practical advice. Measure the amount of time you have, consider in advance how much money you want to spend, and judge how adept you are at costume construction and makeup application. Think about where you will wear the costume. Don’t choose a black costume with limited vision—Darth Vader, for instance—if you’ll be escorting a group of young trick or treaters at night. And shy away from the delicate, hot, or constricting if you expect to be dancing in a crowd or moving in a crowded bar. Large elaborate constructions are better suited to parades and outdoor festivals than to an apartment party, and makeup is more easily negotiated than a mask when it comes time to eat and drink. Costumes that rely on subtle sounds or gestures won’t work at a noisy party or a raucous parade. Thinking ahead will make your investment of time, money, materials, and imagination pay off.

Thanks to Rachel Cox for contributions to this essay.