Gay Halloween Costumes: The Art of Dressing Up + Grindr

At a gay Halloween party, you can show up wearing almost nothing and still have people asking about your costume. A harness and a pair of wings might be the entire outfit. Meanwhile, the guy next to you has spent months painstakingly recreating an obscure pop culture moment, only to end up wearing about the same amount of fabric. Both count. Whether either outfit makes it home that night is another question.

Because for gay men, Halloween has always been about more than finding an excuse to show a little skin (not that we need one). It's an opportunity to experiment with who we are and how we want the world to see us. Maybe you've always wanted to try drag. Or there's a sexual fantasy you've kept behind closed doors that you're finally ready to take out for the evening. And sometimes, you just really want to dress as Kelly Clarkson feuding over a $15,000 mechanical bird at Art of Play. There's room for all of it.

When you're queer, you can spend an awful lot of time considering how you present yourself depending on where you are and who's watching. The version of yourself that comes out at a gay party might look very different from the one your coworkers know, whether that means embracing your femininity, indulging a kink, or simply enjoying the attention when a very attractive stranger can't stop looking at your ass.

With this year's Pleasure Ball: Future Lovers embracing an intergalactic, futuristic theme, there's even more room to let your imagination run wild.

For Broadway performer and returning Pleasure Ball attendee Mikey Graceffa, that means transforming into a robot dog. Specifically, the Tekno Toy Quest Interactive Robot Puppy Dog, a beloved childhood toy. He's quick to distinguish it from the considerably more unsettling robots making headlines today. "These Elon Musk scary robots I've been seeing are scary as hell, and I do not subscribe," he jokes.

Having spent years performing onstage, Graceffa knows how much a costume can communicate before someone even opens their mouth. On Broadway, somebody else determines what character he's playing. On Halloween, he gets to make those decisions himself, including how much clothing the character actually needs.

"For Halloween, you can't think binary: 'I'm gonna be sexy or I'm gonna be scary.' There's so much more of a story you can tell," he says. "It's all about details and specificity."

That dedication to a good reference is something Jeff Dingy, 39, understands particularly well. A few years ago, he went viral among Lady Gaga fans for recreating her Nurtec ODT commercial look. He's since made a habit of trying to outdo himself, including wearing an S-cup breastplate. Last Halloween, he turned an old bodysuit into a sexy dragon costume that left his ass exposed all night—and he's hardly running out of ideas for showing more skin. His patience for wigs, on the other hand, is considerably more limited.

"God bless drag queens because I cannot keep one on for any extended period of time," he admits.

This year, Dingy is making his Pleasure Ball debut as a shirtless, body-painted Monstar from Space Jam, complementing his plus-one's costume. He only had about a week to plan and is juggling two other Halloween outfits, but he's still determined to put his own spin on the character even if nobody else in the room immediately gets the reference.

Ben Abbene, 34, doesn't typically do drag, but he's making an exception for his first Pleasure Ball appearance. His chosen character? "A recently divorced, unemployed, and pet-less Kristi Noem."

Abbene says his Halloween inspiration generally falls into one of two categories: something extremely current or "a hyper-niche reference that only five people at the party will get." This year, he's choosing the former.

But another consideration when he's getting dressed is whether he's hoping to get a laugh or get laid.

"If I know there will be potential hookups or dates, I tend to go for something that shows off more skin and features, rather than a more gaggy/comical option," he says.

And why shouldn't that factor into the decision? There's nothing wrong with putting together an outfit specifically because you know it'll make somebody want to take it off. Other nights, the joke is worth more than the hookup. What makes Halloween fun is that you get to decide what you're in the mood for.

You can put an enormous amount of work into looking like somebody else, only to reveal something very real about yourself in the process.

Graceffa, who attended last year's Pleasure Ball in a revealing gold snake costume, has a particularly simple philosophy when it comes to balancing creativity with showing skin.

"Find the concept and then take those clothes off!" he says. "It's a Grindr party after all!"