Inspired by Kristen Arnett’s own trip down Halloween memory lane, I am here to rate my Halloween costumes of years past.

A lot of trans girls talk about Halloween as a time when they could explore their gender freely — dresses and skirts and make up all under the guise of a mere costume. That was… not my experience. With a few exceptions, before transitioning I would describe my costume choices more as a decades-long performance art exploration of masculinity.

Post-transition things start to get more fun. And by fun I mean making esoteric references that only a select few people recognize. That’s how new friends are made after all.

This list is 1997 to 2022, but I don’t have a photo for every year and some years don’t even remember what I went as! Last year, I was sick, so no costume. But this year I will be making a triumphant return dressed as a certain character played by all-time fave Susan Sarandon.

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1997: Hercules

The first but not the only time I will wear fake muscles and flex. Such a strong little man! Unfortunately I would vomit all over the outfit mere hours after this photo and have to miss trick-or-treating due to the stomach flu.

I’m very cute, but I am not impressed by the realism of the look and Hercules came out in 1997 so it was not a very original costume choice.

4/10 (pre-vomit)
2/10 (post-vomit)

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1998: Bat Man and Robin

It appears like I was going very high concept this year with vampire accoutrement over a Robin costume. It’s a thinker, but it works! Points for originality, points off for the haphazard combo of ideas and the not life-like blue teeth.

6/10

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1999: Woody from Toy Story

Toy Story was the first movie I saw in theatres, so I likely chose this costume out of enthusiasm for the upcoming sequel. I don’t look very enthusiastic in this picture though! Maybe I was overwhelmed by kindergarten Halloween which is kind of like tax season for accountants. Definitely more realistic than my Hercules look, but still out of a bag, so I’m not impressed.

5/10

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2000: Pirate

Another costume out of a bag, another classic archetype of masculinity. The closest I’ll get to wearing anything frilly for many years. But what’s the deal with the sword(?) I’m holding. It looks more like a plastic hammer. Props department could use some work.

4/10

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2001: Nerd

The first of many costumes where I was just a type of boy. I was already being bullied a lot by 2nd grade, so heightening my nerdiness seems misguided to say the least.

3/10

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2002: Injured Martial Artist

This was around the time I realized Party City sold realistic blood and wounds. I was really into movies and loved getting to play with special effects.

My first bloody costume leaned toward simplicity utilizing the outfit I already had from martial arts. The concept was: I lost the fight. I spent all day asking my friends (and crushes?) to fake punch me.

7/10

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2003: Zombie Eating Own Arm

I wish I had a picture of this one! Building on the special effects of the previous year, I created a whole zombie look and hid my arm in my shirt and then spent the day gnawing on a fake arm. (Also from Party City)

8/10

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2004: Arnold Schwarzenegger

As the shortest boy in my class, choosing to put on fake muscles and an uncanny Arnold mask was an inspired choice. Doing it the year after he became governor of my state? That’s political commentary, baby!

10/10

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2006: Old Man

Middle school is a blur, but I do remember one of my costumes: old man. This was another excuse to play with special effects, because I had a realistic beard and bald cap. I remember this costume distinctly because I had a Legally Blonde moment showing up to my crush Ali’s Halloween party with a bald head talking in an old man voice while all the other boys were just wearing various sports jerseys.

9/10

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2008: L.B. Jeffries from Rear Window

Due to a running injury, I used a wheelchair for about the first six months of high school. A perfect excuse to dress up like one of my favorite Hitchcock characters!

Because it was hard for me to navigate other people’s homes at the time, I planned a party at my house. Unfortunately, my friends were very cruel about the whole thing and one of them told everyone I’d changed the party location to his house so I did, in fact, spend this Halloween alone, and did not even finish putting together this costume. Don’t feel bad for me though! I’m sure I spent the night watching a bunch of really good horror movies.

7/10 (costume)
0/10 (friend group)

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2010: Charlie Chaplin

Unclear, what I did with the fresh Halloween trauma my sophomore year, but my junior year was one of the best nights of my high school life! I dressed as Charlie Chaplin alongside my new theatre kid friend group and had a blast. A lot of the other teens about town kept asking if I was Hitler, but I just made fun of their ignorance and talked about The Great Dictator with my new pals.

8/10

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2011: Glam Rocker

The only time in high school I used Halloween as an excuse to be more femme. (One year I wanted to go as Snake Plissken from Escape from New York but my mom and sister said it was faggy.) I was obsessed with David Bowie and with Todd Haynes’ Velvet Goldmine so this costume was an easy one to throw together. I remember feeling really good!

9/10

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2012: Twilight-Spinoff Mummy

Halloween happened a few days after Hurricane Sandy so my dorm was still without power and the city was mostly shut down. Some friends and I went to Times Square to see what it was like totally empty (based on this photo it was not, in fact, totally empty). We had plenty of leftover hoarded toilet paper so I did the concept: What if the popular Twilight franchise was about a mummy instead of a vampire? Basically just an excuse to be a mummy with glittery cheeks and eyeliner.

7/10

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2014: The Boy from Boyhood

I’m so mad I don’t have a photo of this one. I dressed like the boy from boyhood (the teen version who was basically my age) with a minute attention for detail. I was just dressed like a hipster young man which is how I looked on average. But my outfit matched his completely.

The fact that the actor Ellar Coltrane has since come out as nonbinary brings me a lot of joy.

9/10

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2016: Vincent Price in House of Wax

My first couples costume! I wanted to go as Big Edie and Little Edie from Grey Gardens. My girlfriend very much did not want to do that. We were going to the big Sleep No More party since she was in the cast, so I guess I understand wanting to be sexier. Instead we went as Vincent Price from the original House of Wax and she was a wax head. It was a really cool effect that you cannot see because we did not remain friends and I cannot use her photo.

9/10

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2017: Daisies

Oh how much changes in a year! Another couples costume, but this time I’d been out as trans for about six months. This was a really magical night. I felt so good in this outfit and had a lot of fun at a gay dance party.

10/10

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2018: Jennifer from Jennifer’s Body

A couple years later this would be a common costume as everyone came around to admitting Jennifer’s Body is a masterpiece. But in 2018, this was original and I felt very hot and cool. My girlfriend at the time and I did get into a fight because dressing as Needy is not as fun as dressing as Jennifer. But this was when I was in my selfish era so I didn’t really care. (We broke up a few months later).

10/10 (my costume)
6/10 (my behavior as a girlfriend)

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2019, part 1: Piper Perabo in Lost and Delirious

If you thought Daisies was niche, buckle up. During my first year as a lesbian about town, loving Lost and Delirious became a half-joking part of my personality. My sister’s childhood friend/current hot dyke (Libra) recommended it to me which really makes one generous toward a film. Plus Autostraddle’s own Riese Bernard hated it so it was fun to joke about in our new friendship. I love this costume.

10/10

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2019, part 2: Jackie Curtis

Maybe a bit of trans guilt from trying so hard to appeal to the cis lesbians in my life motivated me to throw together this Jackie Curtis costume for another Halloween party. I did spend the evening telling cis girls they should watch Women in Revolt.

8/10

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2020, part 1: Myra Breckinridge

I wish I had better pictures in this costume !! But to be fair it was a pandemic and my two roommates were out of town, so my picture was taken by my roommate’s sister who swung by to help me out. (She was the only other person in our pod.) I added Myra Breckinridge’s strap-on iconic to her iconic look because it was cheeky and because it was a smart way to not have to tuck. This costume deserved to go to a big queer party instead of staying at home.

This was also the second year in a row I chose a costume to impress a crush. I’d watched Myra Breckinridge with someone the first night we hooked up and I wanted to hook up again even though the pandemic had cut our relationship short. (Alas it did not work.)

9/10

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2020, part 2: Shelly from Twin Peaks

I needed a quick outfit I could throw together that was cute but not too forward for Halloween itself. Someone I’d been flirting with virtually for months was finally coming over and my roommates were out of town. My roommate already had this dress so I just made the gun out of duct tape and bam!

We watched Slumber Party Massacre and Slumber Party Massacre II, which possibly came as a surprise to my date, because she maybe thought “horror movie marathon” was a euphemism. She was dressed like Drew Barrymore in Scream which I thought was very hot and cool.

8/10

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2021: Kristen Stewart in Clouds of Sils Maria

I’d been struggling with an eye infection all year, so I had to figure out a costume that worked with my glasses. Look no further than my most esoteric costume yet! I mean, I was dressed as Kristen Stewart that has to count for something. It’s simple but I kind of nailed this.

7/10

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2022: John Wick and John Wick’s slutty dog

Another couples costume! This one with my current partner whose hot face I am allowed to show. We set the bar VERY high with this first outing. I’m sure someday we’ll do another couple’s costume but this one will be very hard to beat.

From vomit Hercules to puppy girl. The trans experience!