For Halloween this year, one young man dressed up as the character he’d always wanted to play: himself.
Growing up in a small city, John* felt he could never expressed himself fully. Looking back on family photos, he says, he can tell his smiles were faked. But after moving to Chicago for college, he started exploring other facets of his identity. In the back of his mind, he knew that Halloween would be the perfect time to debut this new part of himself: a person who identifies as male, but enjoys dressing as a woman.
That’s why this Halloween weekend, John stepped out in his new favorite outfit: a long brown wig, women’s clothing, and black eyeliner winged to the heavens.
Halloween has long been an occasion for people to play with gender identity.
In fact, the whole tradition of adults playing dress-up on October 31 started in San Francisco's decidedly gay Castro District in the 1970s. The Castro Halloween Party featured men dressed as nuns, women wearing mustaches, and all other manner of gender-bending fun. Even before that, in the 1930s, gay men in Chicago were throwing Halloween drag balls that attracted thousands.
Eventually, straight people just joined in.
“Halloween, Carnival, these kinds of dress-up holidays are a moment where people can cross-dress relatively safely,” Louisiana State University professor Catherine Jacquet told Revelist. “…We’re just so limited with this strict gender binary that when when people have an opportunity to go beyond the binary, a lot of people will take it up — not just queer or gay people.”
Jacquet also cautioned that this permission to experiment with gender rarely lasts longer than Halloween weekend. Even the performers at the famous Chicago drag balls, she said, would often be chased down afterward.
But for some genderqueer people, Halloween isn’t just a holiday — it’s a turning point.
In an essay for BuzzFeed, trans writer Meredith Talusan reflected fondly on her first experiments with cross-dressing on Halloween. She, and several other trans writers, explained that the holiday gave them permission to try on a new identity — an identity that ultimately stuck.
For Talusan, the positive response to her Halloween costumes continued to embolden her during her transition.
“I kept coming back to that moment when Lucy told me I looked amazing in her dress, when other friends told me I occupied womanhood so well, those three different times in college when I borrowed dresses for Halloween,” she wrote. “This sense of affirmation carried me through the toughest times – when I lost friends and was discriminated against because I’m trans.”
John has equally fond memories of this year — his first Halloween in drag.
John told Revelist he received compliments not only on his outfit, but on how happy he looked, too. Even the women at the beauty shop he visited were friendly and supportive as he tried on makeup.
John says that based on the positive response, he’ll try out cross-dressing again soon. In fact, he even made a mental note of how his friends did eyeliner, so he could do it again himself.
“This experience convinced me that I can change my gender identity temporarily, if I dress up like I did on Halloween, and not feel ashamed about it,” John told Revelist.
“I wouldn't dress up all the time, but I do intend to do it more frequently, because I love the way my smile looks when I'm dressed up.”
*Name changed to protect identity.
