I Never Did

I never crossdressed on Halloween, I think I was afraid that someone would think that I enjoyed it a little too much so I avoided dressing up for Halloween. Instead I took the safe route, a pirate, Davey Crockett, a solider, etc.

Why Trans Women Have Complicated Relationships With Halloween“I wasn’t dressing up as a celebrity or a historical figure, but rather as an everyday girl. I was presenting as myself.”Posted on Oct. 31, 2015
By Meredith Talusan, BuzzFeed LGBT Staff Writer

“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.
[…]
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.

The article then goes on to talk with other trans people about Halloween.

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.
[…]
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.

This one came the closest to the way I feel. I worried about being outed and I didn’t feel it would be right to crossdress because I saw it as a parody of the way I felt, I was a woman therefore dressing up on Halloween was mocking the way I felt.

Now if I did dress up for Halloween it would be as a nun or a gypsy.