Two queens of Halloween costumes, Drew Burnett Gregory and Kristen Arnett, have previously rated their costumes for Autostraddle, and now it’s my turn. In Drew’s list, she mentions how trans people often use Halloween costumes to explore their gender expression, though she did not. That was absolutely the case for me though, whether it was conscious or not, because as I look at the list of costumes here, I dressed so frequently as men/male characters far before realizing I was trans.
I’m the youngest child of four, so there’s not many photos of me in general, and definitely not from Halloween, so there’s big chunks missing between 1996 and 2010. There’s also gaps in years here because I deleted so many photos from my Facebook after graduation and failed to save them elsewhere. Other photos were posted to my old private Instagram account that I no longer have access to (RIP). I don’t think we’re missing too much though.
1999: Simba from Lion King
I have no idea what I’m holding in my hand here. A leaf perhaps? I don’t remember what it was like to be Simba at three years old but I do remember that my mom handmade this costume, as she did for many of our costumes for Halloween and school plays growing up.
Rating: 10/10 I look cute as heck and it’s giving genderqueer kid.
2000 (and many consecutive years): Harry Potter
I was a huge Harry Potter kid and when I tell people I used to dress as Harry Potter for many Halloweens in a row they’ll ask “Oh were you Hermione?” and I have to be like “No… I was Harry Potter.” This Hedwig stuffy I had was so cute I could velcro his feet around my arm so he’d be perched like a real owl.
9/10: I mean look at the smile on my face! Deducting a point for transphobia.
2010: Playboy Bunny
I was a freshman dating a junior, so I was invited to a Real House Party where half the girls loved me and the other half hated me. I’m pretty sure my boyfriend at the time was dressed as Hugh Hefner in a robe and slippers, but I can’t find any photos. It was pretty bold of us to play into the age difference with our costumes considering I was fully 14-years-old here — but any excuse to wear my Victoria Secret Bombshell Bra!
Rating: 6/10 body was tea but deducting points for age-appropriateness and for those leopard print tights.
2012: Hooters Girl
This Halloween was kind of ruined by Hurricane Sandy’s untimely arrival. I forget what the limitations were but my friends and I weren’t allowed to do any big plans that year and instead stayed in my development trick or treating and probably drinking Four Lokos. I had a real Hooters Girl tanktop from visiting the Manhattan location with my late aunt and paired it with skinny jeans and a leather jacket.
Rating: 4/10 lack of creativity and wasted it on a Halloween I didn’t hang with any boys
2015: Walter White and Jesse Pinkman
My sophomore year of college, my brother came to visit and we were both obsessed with Breaking Bad. My brother is already pretty much Jesse Pinkman in many ways, so it was a no brainer he’d be him. I went back and forth on which Walter White I should be and of course landed on no-pants Walter White in the desert. In this photo, I’m wearing tights and two pairs of tighty whitey underwear because I was so afraid to actually be in my underwear. This mascara goatee would be the first of many, many handmade facial hair for me. This was also only a few weeks after I’d started hooking up with my eventual college boyfriend, and the party we were going to was at his frat. My brother and I did sooo much molly this night — it rocked. He hooked up with one of my sorority sisters.
Rating: 7/10 I should have committed to the bit and shaved my head.
2016: Lola Bunny and Bugs Bunny from Space Jam
This is one of the costumes locked in my old private Instagram account. Trust that I looked cute as HELL in that costume that I made for me and my ex from scratch, just for him to cheat on me with his roommate’s sister that was visiting for the weekend.
Rating: 5/10 cute but not cute enough for him to not cheat on me :/
2017: Jim and Pam from the Office (Company Picnic episode)
I’m not going to lie, this one was 100% my idea, and I absolutely loved it. My college boyfriend had graduated the year before me, so he came up to visit for Halloweekend and I thought this was so cute. Don’t let the innocence of this costume fool you, we were on sooo many drugs and absolutely got in some kind of screaming fight outside a frat house.
Rating: 4/10 basic as fuck
2017: Mia Wallace and Vincent Vega
WE BOTH LOOKS SO HOT IN THIS COSTUME. Truly so hot and so good and not enough 20 year olds attending SUNY Oswego had seen Pulp Fiction to appreciate this costume. That bob and bang wig was sooo cunt. The most annoying thing about this costume was I wanted to smoke cigarettes all night so bad, but my college boyfriend was so anti-cigarette despite regularly doing pills behind my back (lol) he got mad at me for smelling like cigarettes at the end of the night.
Rating: 10/10 I can’t lie it was a killer costume and we did the dance and everything.
2018: The Big Lebowski
The Big Lebowski is one of my favorite movies, and The Dude is one of my favorite characters ever. Luckily, my ex Vic was just as enthusiastic about this couple’s costume as I was and I really think we assigned the roles accurately. She did a reallllly good Walter. This costume was specifically for her hometown friends’ party, and I think we were a crowd favorite. I engineered my milk carton so that I could put my beer bottle inside and still drink from it, which was pretty cool if I do say so myself. This pic doesn’t show it well, but I was in a full floor length bathrobe.
Note: I have not covered up Vic’s face because when I texted her to see if she’d be okay with me using these images, I offered to cover her and she protested “then people will think there’s bad blood!” and that’s on being friends with your first lesbian ex <3
Rating: 10/10. We looked great, it was comfy as fuck, and may or may not have pushed me along on some kind of eventual gender journey.
2019: Dumb and Dumber
I remember having to concede to this costume idea because Vic really wanted to do it. I didn’t have any opposition to being Dumb and Dumber as a concept, but I really wanted to do it in a more literal way with oversized suits and not in a “girl version” way. But alas, that’s what we did. It ended up being a hit at the party we went to at her hometown friends’ house. We couldn’t find an orange cane for her, so I wrapped it in orange electrical or duct tape.
Rating: 5/10 really fun couples costume but I stand by that it would have been better if we had just worn suits.
2019: Bob Ross
Halloween while bartending is always a little bit tricky because you want something fun but practical. I was in grad school at the time and bartending at a lesbian-owned restaurant and cocktail lounge (shoutout Lost Dog Binghamton) where they’d play random things on the TV after hours for the drunk or high customers in the lounge. Sometimes it was a crackling fireplace or the POV of an Amtrak train, other times it was Soul Train or Bob Ross. I had pretty much the whole outfit needed for a Bob Ross costume and just had to get the painting supplies and wigs.
Rating: 8/10 it was great to be in jeans behind the bar and it was a little treat for the regulars at the restaurant.
2019: Eleven (bitchin’ era)
Okay so I had literally just done the Big Chop the day prior and received some immediate comparisons to Millie Bobby Brown. It was also my first few days — let alone first Halloween — with short hair and wasn’t entirely sure what to do with it. Reflecting now, I’m like, okay, why would I do this character costume two years after its relevance? But I think it was out of necessity in a time crunch.
Rating: 9/10 honestly proud of this one and the dedication to doing a photoshoot in my neighborhood liquor store for accuracy. Docking a point for being late.
2020: Dr. Alan Grant ft. Bo as Velociraptor
I have been in a few different relationships where I have requested me and my partner be Dr. Alan Grant and Ellie Sattler, and every single one has said no. Whether it was too nerdy or not cute enough or “I haven’t even seen that movie Motti,” no one was getting down with Jurassic Park. Well, I was single for Halloween in 2020, the world was pretty much shut down, and I had quite literally everything I needed to be Alan Grant in my home already so I finally got to do what I wanted.
Rating: 7/10 I think I did a good job but this costume is just not as good without either Ellie or some other character or dinosaur from Jurassic Park. Kristen and Kayla did it right for their 2023 costume.
2021: No Costume
I think I may have had COVID this year?
2022: Carmy from The Bear
This year, I was back in New York, bartending at a Colombian lesbian restaurant, and single. I didn’t put much thought into my costume because I knew I was working the closing shift and therefore wouldn’t be making any parties. The head chef at this restaurant only used the blue aprons like in The Bear, so I showed up for my shift in a white tee and black dickies, threw on the apron, and had a co-worker draw on Carmy’s tattoos with a sharpie.
Rating: 7/10 the gay girls loved having a masc lesbian Carmy serve them drinks all night but if I’m being honest, it’s some of my laziest work.
2023: BJ and Judy Gemstone
My girlfriend and I LOVE The Righteous Gemstones and are particularly obsessed with BJ and Judy Gemstone. The episode where BJ gets baptized to show his commitment to Judy and her superreligious family kills us, and we knew we wanted to dress up as that specific episode when we first started brainstorming. It took as a WHILE to find a dress close enough to Judy’s and even longer to find an accurate-ish outfit for BJ. We ended up assembling it ourselves, pulling each individual item from different places and modifying them to work together.
Rating: 10/10 this costume was so good the actors who play BJ and Judy reshared our posts
2024: Chappell Roan and a Passenger Seat
I mean… come on. Chappell Roan and a Passenger Seat (from the song Casual) is one of my proudest ideas yet. I’ve spoken pretty extensively about this costume after it went viral for the whole “I Hate Gay Halloween, What Do You Mean You’re ____” trend. My girlfriend, Britt, knew she wanted to somehow dress as Chappell Roan since she’s halfway there with her hair anyway, and I had the crazy idea to be the passenger seat she references being knee-deep in. I constructed the passenger seat myself from scratch and had so much fun putting it together. We turned heads everywhere we went that night, especially the multiple trains we had to take to our friends’ party in Brooklyn. It’s so funny that for most of these costumes, I dressed up as men, but as soon as I started identifying as a man, I dressed up as an inanimate object. I’m sure there’s something to dissect there.
Rating: 100/10 instantly iconic costume, will be referenced for decades to come.
so many iconic looks here and also i didn’t know that there were people in the world who haven’t seen jurassic park
yeah this is upsetting!!!!
Love these. Can’t wait to see which inanimate object you dress up as this year, lol.
I used to do something similar, but from the other side. Back when I played a lot more TTRPGs, a friend once asked why I always played female characters. Being deeply in the closet at the time, I shrugged and said nobody else was playing female characters so I felt someone had to. Of course, now I know better.
I actually bumped into the person who asked that this past weekend. If they recognized me at all, they didn’t say anything. Twenty years and fifteen years since starting my transition can do that.