The Transformative Magic of Halloween

Halloween Jack-o-lantern
By Ashley Altadonna
For most people, Halloween conjures up images of spooks and spirits and memories of trick-or-treating, costume parties, jack-o-lanterns, and scary fun. For those of us in the trans and non-binary community, Halloween may also have an added significance. October 31st may be the one time of the year where we can freely explore our gender identities and be our authentic selves. It's a day where gender norms are cast-off and we can dabble in being the version of us that we hope to be.
Still for some, the fact that Halloween is an excuse to cross-dress, or even pretend at being trans can feel as though our existence is a joke and a painful reminder that some still don't take our identities seriously. Love it or loathe it, Halloween has played a unique role in the experiences of many trans and non-binary people's stories. Since the pandemic has scared away many of this year's Halloween plans, we thought we would share some trans and non-binary recollections of All Hallows' Eves gone by.


"Growing up in the deep South I didn't have much exposure to the LGBTQ+ community. Halloween allowed me to live a night as the woman I wanted to be without fear of judgment. It was a night of escape from a confusing world which I thought was completely against someone like me. It took me until I was in my late twenties before I even began experimenting." 

– Christine (She/Her/Hers and They/Them/Theirs) 


Photo courtesy of Ryan Cassata

"Breaking gender stereotypes is often criticized in our culture.Transphobia often makes it scary for many trans people to dress in ways that make us feel like ourselves. Sometimes the only day that trans youth can dress in an affirming way is on Halloween. I remember dressing up as different baseball players that I liked, Slash from Guns N' Roses, Edward Scissorhands, an orangutan, a princess, a witch, basically anything I liked at the time. 

“For me, I got to dress how I wanted on Halloween but also basically every other day of the year aside from my school uniform. My parents were fine about my backward baseball cap that I wore since I was super young. They were fine with me dressing in baseball jerseys and jeans. Long before I came out. I was lucky to have that freedom. Not just on Halloween, but all the time."

– Ryan Cassata (He/Him/His)


"The first time I wore a tie wasn’t a formal occasion. No, those affairs called for a scratchy, stuffy dress complete with buckled white shoes and delicate socks adorned with embroidered flowers, and lace. Always lace. Try as I might – which was neither very often nor with very much effort – my body belied every marker of its girlhood. When I wasn’t in a dress, the inevitable question came: 'Is that a boy?'

“The year I was disciplined for disrupting class with a group of boys (with the ironic and inane assignment of repeatedly writing, ‘I will not flirt with boys in class’), was the same year I was allowed, with great parental hesitation, to set foot outside on Halloween outfitted in a tie. Like JFK, whom I’d recently read about and instantly admired for his good looks and charm, I exuded confidence and commanded respect. My tie was as much my battle flag as it was my armor. As I fielded the unexpected inquiries, I began to feel a new and deeply authentic sense of self. ‘Why are you dressed like a boy?’ Because I can."

– Shelley Gregory (They/Them)


"One year when my brother and I were very small, my brother told my parents that for Halloween he wanted to dress up as a businessman. He cut up a cardboard box and rigged it with rope to have a desk hanging around his neck, complete with a stapler, a manilla folder, and a plaque that had his name on it. He wore a button-down shirt with a clip-on tie and if it wasn’t for his tennis shoes, he would have looked like one of my interns. Today, he heads a nonprofit, and while I haven’t seen his office, I expect it looks a lot like his costume.

“I wanted to dress up as Carmen San Diego. My mom had a red hat and a red tweed jacket that looked close enough to the part. When I picked out the outfit, my mom told me that I made a great Sherlock Holms and introduced me as such at every house we visited. I didn’t understand at the time why I was so jealous that my brother got to dress up as what he wanted to be."

– Addie Lipson (She/Her/Hers)


"My earliest memory of Halloween was when I was seven; it was 1985 and Madonna's 'Like a Virgin' was all the rage. My Brownie troop (Girl Scouts) gathered after school one day to talk about costumes and everyone but me planned to dress like Madonna. When my parents asked me what I wanted to be, I chirped 'Skeletor!'
“They obliged my wish and I arrived at school shrouded in clingy blue plastic and shook my toy staff at the row of Madonnas. I honestly don’t know what people thought, and I had no sense of shame or remorse to be dressed as a villain that was different from my assigned birth gender. As a gender non-conforming child, my parents never forced me to act or dress in overly feminine ways. It’s only in retrospect that I have any awareness that many of my affinities and choices were 'gender unconventional.' Photo courtesy of Andrew Sempos-Anastasia

“The blissful banality of my previous Halloween experiences ended last year when I let my four-year-old daughter choose my Halloween costume. She decided quickly I would be a mermaid. Because I grew up with only the internalized shame of living awash in gender normativity, I thought I would feel comfortable being whatever gendered creature my daughter conjured. Halloween evening, I wriggled into my mer-skirt and put on my long wig. My wife did my makeup and when the look was complete. 

“I walked by a mirror and froze. In the background, I could hear my daughter squeal with delight, but I was struck by a deep dysphoric feeling. After fourteen years of living in a body that felt pretty comfortable, I mistakenly thought I’d be relatively unfazed by a night of harmless cross-dressing. I was immediately flooded with memories of high school dance fails where I’d tried, in vain, to convince everyone--especially myself--that I could ‘pass’ in what always felt like feminized drag. I remember folks taking pictures and laughing with me; I was quick to explain wherever I went that my daughter had chosen my costume. I reached for the sheepish shoulder shrugs and fake-apologetic facial expressions I’d seen modeled by toilet paper commercials where a cis-het dad was plied into attending a costumed tea party with his daughter.

“Not wanting to participate in that subtle, scripted denigration of women, I returned to the party we were attending and tried to hide my discomfort. I felt completely alone in that moment; out of place anywhere on the night where anything goes. Perhaps many trans people have an acute awareness of our experiences being fetishized for one night only. For me, I learned that in spite of having a family that affirmed my genders over time, I’m still vulnerable to the inexplicable and often unpredictable experience of dysphoria.”

– Andrew Sempos-Anastasia (He/Him/His)


"White face paint. Drawn-on fangs with a drop or two of blood. Slicked back hair, with a penciled widow's peak. My mom disapproved, 'You know, vampires can be girls, too.'

"'Well, yeah, but why would I want that?'

“Luckily, by the time my mom tried to lock me back into my usual gender cage, I had already figured out a costume. All I remember of it now is a faux velvet suit jacket and much more importantly, how I felt. I knew perfectly well I wasn't as dashing or debonair as Lestat, but in that suit, I felt 'right' in a way that would take me many more years to understand was my gender identity aligning more closely with the way I was dressed.

-Ben Andert (They/Them/Theirs)


"It was in 1999, and every store was stocked with Disney's Tarzan paraphernalia. At the time, I was eight years old and already fully aware that my assigned gender did not match my psyche. My parents are firm believers in being who you are, but my father was very open-minded to allowing me to discover the 'who' in me. My father asked me, 'What do you want to be this year for Halloween?' I replied with a very quick 'Tarzan', as I banged on my chest. I connected with the film immediately. I found myself relating to Tarzan, trying to find my placement in society. It was also at this moment that my heart learned that family does not have to be biological. Tarzan allowed me to stand up against my fears of hatred and being different (wanting to be a boy) and to always do what is right.

"’Well, I'm unsure how that'll work, but let's see what the store has’, my father said with the uncertainty of finding a ‘girl Tarzan’ costume. We went to the local department store and I grabbed exactly what I wanted: a Tarzan costume that consisted of one brown wrap-around cloth and a plastic vine necklace. ‘Alrighty then,’ my father said with confidence. I was so excited, not just because it was the most popular movie of the time but simply because I was able to be a character in the gender I prayed to one day become. The costume became a long-term dress-up prop, along with many other ‘male’ roles. 

“Over the years, I always found a way to be the ‘male’ superhero, ‘male’ vampire, ‘male’ basketball player, a cowboy, and even a ‘male’ rapper. My Christian mother would always give me the side-eye, but she did enjoy how creative and detailed I could get each year. As I got older and transitioned, I found that Halloween became a time that I could be more feminine in my costume choices. To this day, Halloween is my favorite because I get to be creative and live authentically.

“Each year The Dezjorn International Foundation Inc. hosts an annual Halloween Party for youth, to provide a safe-fun-space for LGBTQ children who feel like the young Dezjorn did back in 1999, dreaming to look like Tarzan. Remember, clothing has no gender and you can be whatever your creative mind wants to be! Always BE YOU!"

– Dezjorn Gauthier (He/Him)

 Happy Halloween!