“You look so good as a girl,” my friend Lucy said after I borrowed one of her skin-tight black mini-dresses for Halloween. “I hate you.” I looked in her full-length mirror as she pointed out how thin my legs were, and how I had delicate features that only got prettier as she helped me apply lipstick and mascara.
That was the first night I dressed in drag — or, what I thought was drag at the time — for our annual Halloween Drag Night at Adams House, my undergrad dorm at Harvard. Drag was never something I particularly craved, especially since I incorporated feminine clothes into my wardrobe on a regular basis, but more in the vein of colorful tops and scarves rather than dresses.
When I came into our dining hall and found most of the other people dressed across gender, the comments about how “convincing” I was continued. While there were certainly attractive drag queens among our young group, there was something about my average build that didn’t turn me into a larger-than-life theatrical version of femininity, but just someone who belonged with the women.
It wasn’t until I began to transition, six years later, that I came to understand what those early experiences meant to me. 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. This sense of affirmation carried me through the toughest times – when I lost friends and was discriminated against because I’m trans.
Since Halloween is the one day of the year when those assigned male are allowed to dress as women in public, I’ve known for a while that it has a significant place in the lives of many trans women and non-binary femmes. But what I didn’t realize, until I actually asked some friends what Halloween meant to them, was that there are huge differences in how Halloween has affected our lives. Here are some of their perspectives.
Sarah McBride, communications manager
For the first 21 years of my life, Halloween meant the opportunity for the costume to come off. I guess my relationship with Halloween was the exact opposite of my cisgender friends. For 364 days I wore a costume, but Halloween was the one day a year where it was remotely acceptable to explore my gender expression and identity. The Halloweens where I mustered up the courage to explore my gender resulted in the most boring "costumes" possible. I wasn't dressing up as a celebrity or a historical figure, but rather as an everyday girl. I was presenting as myself.
The beginning of the end of my time in the closet was Halloween 2011. I was serving as student body president at American University and decided, along with two guy friends of mine, to "go as girls." And so I went out as me.
I remember feeling so free when the first pictures of me as a girl went up on my Facebook that night. Almost immediately the responses were life-affirming. It was that night where I first realized, "Okay, I can do this. I can transition. I can make it." Almost no one knew they were seeing me for the first time.
Two months later I came out to my parents and started to transition. My journey would have been dramatically different had it not been for that one night a year where it was socially acceptable for a "straight, cis guy" to push the gender barriers. Halloween gave me the room necessary to explore without as much fear.
Benjamin Mintzer, university administrator
The significance of Halloween for me boils down to this picture my mom took of me when I was 16. At the time, I wasn’t even aware that transgender people exist, even though people had been identifying me as a girl since I was a kid. My family always “corrected” those people who took me for a girl, and that was how I internalized that being a girl was something I shouldn’t be.
But that one Halloween night was the exception, when I dressed up as a girl for a high school party. I was incredibly anxious leading up to the moment. I spent about a month planning: window shopping for the perfect dress, befriending the makeup counter beauticians at the mall, and budgeting my meager teenage finances. That Halloween gave me permission, in the conservative political climate of the suburbs, to subvert the identity assigned to me. Being welcomed by my friends, and even hit on by straight male peers, made my identity feel legitimate and accepted, even for one night.
My mother took this picture when I came home from the party. I haven’t felt closer to her since. And sadly, I don’t think I ever will again, because of how hard it is for her to accept my gender-nonconformity.
Jasmine Rodriquez, writer and actress
On Halloween 2004, ten days shy of my eighteenth birthday, I dressed in drag — really bad Wal-Mart last minute costume drag. Then I met up with two girls from work just to hang out in the park. This was in Tampa, and ignorant of the dangers awaiting a lonely boy in drag in that particular neck of the woods, I walked home. As I neared the entrance to the subdivision where I lived, a red pickup sped past, a beer bottle whizzing past my head and landing in the grass. I stayed as calm as I could, walked all the way home, and didn’t say a word about it.
2006 was the year I began transition. On Halloween, I got dressed up for a nightclub, and my friends and I got plastered. I don't remember it at all so it must have been great (I hope). After that, I used Halloween as a way to play into the "sexy costume" ideas, one year as Catwoman in something I'm too shy to wear now.
Lately, I've begun to have less time for Halloween because of work. Now, for the first time in a few years I'm off for Halloween, and I'm going as a nudist on strike because the holiday that once held so much significance for me just before and during my early transition has somehow snuck up on me. I suppose now that I no longer feel as though have only one day of the year to be free, it has lost its appeal beyond staying in and watching movies.
K.
I transitioned in my teens and am not public about being trans, or “stealth” as people call it. I feel a little weird that I’ve never cross-dressed on Halloween, either before or after transition. It was one of those trans woman checkboxes I never went through. I was constantly worried about people seeing a man in drag or just a guy in a guy's costume.
Halloween is the patron holiday of drag queens already, so even though young trans women also use it as a time to dress up, I feel like going out in highly-gendered costume is putting yourself on blast. Think of when cisgender people wear cross-gendered costumes: it’s the exact opposite of passing. It’s parody. Short of being read as trans while being out on a date and dressed up, nothing else sucks more.
Christopher Soto, poet
The first time I wore a dress in public, I was nervous. I performed femme as a character, flipping my hair, popping my ass, strutting my walk. The first time I wore a dress, femme became a comedy, a character, a joke to perform. I was scared of being seen. Femme was not a presence to inhabit, because it was something to be ashamed of.
Now, I am thinking about the transphobia that cis-men reproduce when wearing dresses on Halloween, the way that trans people (and cis women) become characters to mimic (like zombies and ghouls and mermaids). Trans femme existence is only possible when it is a costume. I am thinking about how that site of violence also becomes my one day for liberation. Nobody will look at me and say “WHAT THE FUCK IS THAT DUDE DOING IN A DRESS?” They won't know that I'm not in costume.
Hannah Simpson, medical student
For me, Halloween was Plausible Deniability Day. It was the one time I could dress as a girl and it was okay. The first time was in college and I had bought heels at a thrift shop and a dress I hoped might fit. I went to marching band rehearsal in my "costume," but nobody else was even wearing a costume. Everyone else had theirs packed to take out later at the party. I guess I was too excited.
A few years later I came fully dressed to work at a campus lab on Halloween Day. Nothing flamboyant. nstead, I dressed as if I had always been female, picking a work-appropriate skirt and boots. A few coworkers knew my truth, but my bosses didn't. Half the thought it was funny as hell, the rest found it tremendously unprofessional. For me, it just felt natural, and I knew nobody dared to raise a huge stink.
With each year I got more confident going out in public and posting pictures via Facebook. I felt if I lessened the shock it'd be easier and safer. If people did question me, I'd be able to turn the tables and ask them why they hadn't known my "open secret" all along.
Halloween was a gateway. It was the chance I could wear women’s clothes as a costume, even during the day, when nobody else was wearing their costume yet. In reality, I wasn't either.