You should not invite me to your costume party
If you, like me, hate Halloween, I highly recommend both scheduling your physical house move for that day and relocating to a neighborhood with nary a child in sight. I bought no candy, have no leftovers, had no weird issues with dogs barking and didn’t have to pretend to have holiday spirit for an evening that is designed to maximize my discomfort by combining all my least favorite things: awkward conversations with strangers about superheroes, begging and costumes.
I can’t pinpoint the beginning of my dislike of this holiday — and costumes most especially — since my Mary Poppins-esque kindergarten teacher, Mrs. Exon, gave me the most magical Halloween memories early on where every day in the month of October, she turned just a tiny bit more into a witch. I think she started with one black fingernail and it progressed until her skin was green and she had a prosthetic nose. Incidentally, the other highlight of kindergarten, when we walked through town with monarch butterfly wings to mimic their migration path, also featured costumes… so it’s unclear why with such a spectacular start in life (I dare anyone who had my kindergarten teacher not to fall in love with learning) I moved to a decidedly anti-costume & Halloween stance.
My top possibility is just annoyance and general bitterness of the entire Halloween experience in the Northeast because it was always just cold enough that we had to wear coats and it was often raining so no one could see your costume and then… what’s the point?
It may also have been my high school group costume as the Babysitter’s Club where I was smacked in the face with the reality that a tall, bossy and non-athletic brunette doesn’t fit in the club at all. Kristy? Bossy and brunette but athletic and short. Dawn? Blonde Californian & vegetarian. The latter attribute is obviously not relevant to a costume but certainly indicative of a vibe I can’t pull off. Mary Ann? Probably my closest chance but we had others in the group better aligned with boring and mousy. Obviously everyone wanted to be Stacey but, again, blonde and worse, cool.
As a result, I, a very pale and tall mathlete of Western and Northern European descent, was forced to go as Claudia Kishi, the artistic Japanese-American who can’t spell. I believe I wore black and white paisley tights, a blue and purple paisley dress and a disgruntled attitude about my lot in life.
I certainly had other uncomfortable costume experiences including heading out to my brother’s law school graduation in Chicago. Just a few days before boarding my plane, my brother called to say that his friend’s graduation party that we’d be attending was a costume party. I was going to be flying there straight from work, had no time to think about a costume and told him that I would be dressed as an apathetic entry level New York ad agency staffer: in jeans and a black shirt. Sadly, it was pre-Theranos so I couldn’t just rebrand as a brunette Elizabeth Holmes.
I was picked up at a subway station by one brother in a pale suit à la “Miami Vice” and the other in a white Elvis costume that I was quickly informed was inappropriately tight (read: stretched thin enough to be transparent) and, as a result, he had to wear a neon Speedo underneath. We arrived at the Irish-American Cultural Association of Chicago where the first floor featured a raucous group of seniors playing Bingo and the second floor held a significantly less raucous crowd for a graduation/costume party that no one else was in costume for. In fact, several were in formal attire — including one man in full naval dress uniform. I was simultaneously inappropriately dressed for three parties.
Regardless, I have since learned that there are many hardcore costume/Halloween people and somehow, like outdoorsy folk, have befriended several of them. Costume and Halloween people are easy to spot in costumed-circumstances because their attire shows such effort and expense you can’t miss them but in normal everyday non-costumed situations, you may be surprised to discover who’s hiding a robust wig collection at home. I will often throw out a generic question on Halloween to get a general pulse of the audience before coming down too hard on my “only troubled adults are into costumes” stance and citing the fact that the entire plot of “Capturing the Friedmans” was uncovered because someone wanted to go deep into the world of Upper East Side costumed children’s party entertainers (i.e. clowns).
Unfortunately, there is a truth that the Venn diagram of “costume people” and “people who work at start-ups” has heavy overlap although some of these people are far more committed than others. I regularly think about a woman I worked with who, on a business trip, went into great detail describing her Halloween wedding when she and her husband-to-be would be in full prosthetic makeup (she would not reveal her costume as she didn’t want to spoil it) and all guests were required to come in costume. She shared that her mother was very upset that she was being made to dress up as a pirate and I found myself just imagining trying to tell my mother that she didn’t need to worry about finding the right dress but should think about a comfortable eye patch. I think I asked at least four variations of “so if someone doesn’t come in costume, even if it’s your grandmother, they won’t be allowed into your wedding?” She confirmed that if a guest was not in costume, no matter how close a family member, they’d ruin all of her photos so it was paramount that everyone follow the dress code.
Incidentally, this same person was an aspiring Instagram influencer with a big commitment to food photos so she ordered a ton of food at this work happy hour, took pictures pretending to eat it, didn’t eat it and then announced she was leaving to meet a stranger from her Instagram DMs and skipped out on the rest of the evening. Somehow my early judgmental questions must have made an impression because she changed her privacy settings on Instagram so I could follow her but not see her Teen Wolf-prosthetic faced wedding photos. Alas, privacy settings are no match for screenshots and group texts with people equally petty so I didn’t miss a single thing.
Independently of people at start-ups being disproportionately into costumes in their own lives, they allow it to trickle into corporate events that regularly feature mandatory costumes. Full company bonding events have involved breaking into teams and each team has had to come up with a team name, theme and matching dress. Bless the group to which I got assigned at one event where we agreed to just say we were Seal Team 6 and told everyone to find a camo t-shirt, headband or hat. Moreover, thank goodness I was not on the team at the same event forced to dress as gladiators with headpieces and togas. One off-site required 80s attire and it was obvious while waiting in the lobby that three other people had all used the same “80s costumes for women” Amazon query and purchased the same outfit:
Since I’d received some performance feedback that I needed to bring positive energy to all events — including social and costumed ones — I knew I couldn’t look like everyone else and ran into the Vegas hotel gift shop looking for any accessory to set me apart. I was able to spend $55 on a sequined baseball cap so I could look like I tried. There’s been an incredible return on that $55 because once the pandemic started and everything went on zoom, any time I needed to seem “fun” I could just wear that hat. Apparently one’s attitude outside of work at corporate events is a reflection of how one feels about company culture. But truly… can’t you enjoy a company and its culture and appreciate its product roadmap and just… want to do your job? Can’t that culture of inclusion include people who want to wear normal clothes?
My compromise in all of this is to spend time and energy (but not money) in the world of low ROI costumes from going as a swing state one election year (red & blue striped shirt with felt letters that spelled out “Pennsylvania” on the front and “Swing State” on the back) to telling someone I’d go as Brad from “Hey Dude” to an 80s/90s television theme party which just meant I wore cowboy boots and tied a bright bandana around my neck. In my defense, I would have gone the extra mile to French braid my hair but it was too short and I never learned how. Unfortunately, when you combine a low effort costume with a judgmental face (not to mention the name Karen), it always looks like you’ve got a bad attitude.
Better to hide inside with the lights off or move to a neighborhood where no one cares.