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How to Dress (or Undress) For Fantasy Fest in Key West

Looking for costume ideas for Fantasy Fest? We offer tips on how to create an outfit perfect for the Florida Keys' biggest party.

By Brooke Morton

January 6, 2014

You want to make a splash, bare some bits and have a good time. Here’s what you need to know to be prepared for Florida’s wildest Halloween parties — and possibly win a costume contest or two.

How to Dress (or Undress) For Fantasy Fest in Key West — Contrary to rumors and contrary to what you might (OK, will) see on the street, showing your full monty could attract unwanted police attention. It’s still illegal. Fantasy Fest officials create a “fantasy zone” that spans two blocks wide and the length of Duval Street. It’s marked with signs and pink caution tape. Here, breasts can be exposed so long as they sport pasties and/or paint. Sheathe your bottom bits with at least a thong.Credit

How to Dress (or Undress) For Fantasy Fest in Key West — Stay away from ready-made costumes, especially if you’re hoping to spark conversation. Unique stands out — and it’s more fun. I met a trio of girls who had created pixilated cardboard cover-ups giving the impression that their nudity had been blurred by the media. Another woman covered her bits with various gray paint chips, honoring that pulpy but popular novel.Credit

How to Dress (or Undress) For Fantasy Fest in Key West — Bring money: Airbrushing the front of your torso costs $100. The paint will last through a shower so long as you lose the loofah. That said, most women who come to play want to parade a different look each night and they’re willing to pony up for the privilege. This might explain why on Saturday I had to hit up four ATMs before I had crisp bills.Credit

How to Dress (or Undress) For Fantasy Fest in Key West — This year, I wasn’t brave enough to get my ladies airbrushed, so I wouldn’t have learned that the art can leave an impression on more than just the crowd. I chatted with Bill Hoebee, a Key West-based TV and radio personality, and he told me that most women aren’t diligent about removing the oily paint before bed. It’s easy to ruin sheets this way, and hotels fine for this.Credit

How to Dress (or Undress) For Fantasy Fest in Key West — If you’re going to be in the pedestrian parade and walking with friends, incorporate a keg or cooler into the costume. I loved the group dressed as “Sharknado” not simply because one participant was on a bike, but because the tornado itself disguised the keg.Credit

How to Dress (or Undress) For Fantasy Fest in Key West — Textiles — that is, people who wear clothes on the regular — often make costumes by adding the word “zombie” to anything. The clothing-free community creates costumes by adding the word “disco” — as in disco alien, disco Smurf and disco Napoleon. It’s possible this is just a ploy to incorporate more sparkles and glitter body paint.Credit

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10 Things to Know about Fantasy Fest in Key West, Florida

Key West, Florida, gives us Halloween on steroids, but it's more than that. Especially for women, it's a relatively safe, encouraging environment to be on display for those who so choose. Those who bare receive overwhelmingly positive feedback. Think about it: It's rare that women — and men, too — can be so free without a freight train of consequences. Here, it's safety in numbers because, for better or for worse, nearly everyone is doing it. — Brooke Morton

How to Dress (or Undress) For Fantasy Fest in Key West — You most likely won’t win a contest, but you’ll enjoy the guesses of strangers if you don’t know in advance what you’re dressed as. I asked a few folks who answered “ask me again at the end of the night” or “you tell me.” Don’t think of this as the this-is-my-costume T-shirt. You do have to put in some effort, namely gathering a few suggestive items. I saw a man in a clear shower curtain cape and a lot of polka dots. Another wore just a toilet plunger.Credit

How to Dress (or Undress) For Fantasy Fest in Key West — Even though this crowd accepts pretty much anything, weirder is not better when it comes to costumes. Bill Hoebee, a Key West-based TV and radio personality who has hosted more than 100 Fantasy Fest costume contests, shared what works to win. He says that it’s better when people understand your costume right away. “Keep in mind these people have been drinking,” he says. “If you have to explain what you are to a drunk audience, you’re not going to win.”Credit

How to Dress (or Undress) For Fantasy Fest in Key West — Remember: Confidence is a costume.** I**f you’re hot — like crazy hot — you can get away with wearing little more than nothing. One prize-winning contestant at the Smokin’ Tuna Saloon’s costume contest wore only a handful of well-placed strips of black electrical tape. ****Credit

How to Dress (or Undress) For Fantasy Fest in Key West — Of course audiences cheer loudest for the hottest women, but being in shape isn’t always enough to take top honors. Consider how the Smokin’ Tuna Saloon’s contest ended. Several model-hot women wore “costumes” that weren’t taxing anyone’s imagination, but the big winner of the night was a Cirque du Soleil performer dressed as a lion, performing on stilts. His ability to curl, rotate and roar to life wowed — and spooked — the crowd. This proves that at Fantasy Fest, as with the real world, looks can land you the spotlight, but talent lets you keep it.Credit

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