How To Do Halloween As A Grown-Up Man

Advice on getting through the scariest night of the year without sullying your good name.

It's Saturday, October 26, 11:45 p.m. You're standing next to your friend's freezer, from which he's dutifully attempting to extricate ice with a knife, while a sticky orange drink is warming in your hands. Half of the party hasn't bothered with fancy dress costumes, the other half are a weird assortment which includes a recycled Hillary Clinton pantsuit from 2016, Jafar from Aladdin and, wait, is that a man dressed as the prorogation of parliament handing out Doritos?

Did parties always make you feel so sad? And wasn't Halloween two days ago? Why are you standing in Camberwell, an area not famous for its NFL team, surrounded by a zombie cheerleader troupe?

Something happens in that moment when you're no longer a child, but also haven't produced any yet. You're uncomfortable at the idea of buying a ticket for Spooktacular Sounds at Ministry of Sound, but not quite ready to invest a Paw Patrol costume for your child, fail to convince them to wear it, and do three hours of trick or treating with them wearing your washing-up gloves as their outfit.


So how to enjoy those in-between years? There's no wrong way to do Halloween—aside three hours of solo apple bobbing—but trick or treating is something that should always remain firmly in your childhood. In Chesapeake, Virginia, trick or treating over the age of 14 is subject to an arrest, a fine, and/or jail time. While the reasoning behind this was a spate of violence in 1968, we applaud this town for sticking to their guns for the 51 years since.

When it comes to going out, exercise the same amount of caution you would with any party. You don't need to say yes to a squat rave, house party or cheese tasting just because it's October 31st. There can be profound pleasure in willingly sitting out events like Valentine's Day, Halloween or New Year's Eve. Just don't be the buzzkill who bores on about why you're 'rejecting the commercialization of a pagan festival'.

Should you choose to partake, perhaps your greatest hurdle to overcome is finding an outfit that signals you're a sophisticated, cultured man, but one who doesn't feel the need to use their costume to prove something about themselves.

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In some senses, men have it easy, with iconic characters from Pulp Fiction, Twin Peaks and American Psycho all easily achievable with a suit you're not too attached to and a bottle of fake blood. They also don't face the problem that the Halloween costume industry has created for women, that all costumes—even toothless wenches or Angela Merkel—must be made sexy and come with a hot-pant and crop-top variations.

But, where does that leave them? Trying to woo liberal ladies by dressing as the death of democracy? Or spending hours creating an authentic ax wound on your shoulder to appear genuinely terrifying?

Cinema is usually a reliable indicator of which costumes will be popular in any given year, as anyone who attended a Halloween party in the year of The Dark Knight can attest. Expect as many clowns this year, indebted to either Todd Phillips' Joker, or the It Chapter Two's Pennywise.


Instead of being one of three sad Jokers at your friend's shindig, might we suggest the more arthouse option of dressing up in a red jumpsuit and carrying a gold pair of scissors, à la Jordan Peele's Us. No need to smugly comment on how his horror films are a chilling social commentary, brandishing those scissors should get your message across clearly enough. Zombie versions of The Irishman cast—Robert De Niro, Al Pacino, Joe Pesci, and Harvey Keitel—are a clever way to show you're aware of the death of Old Hollywood, though does have the potential to come across a touch ageist.

Then there's Instagram to consider, which has made the Halloween party infinitely more horrifying by turning every costume into a quiz on your knowledge of niche internet culture. In recent years, Halloween 'fits that reference memes have become memes themselves; see the CNN producer dressed as the children who interrupted a political scientist's BBC interview, or friends going as both versions of The Dress. Are they blue, or are they gold? Are they boring, or completely insufferable?


If you are tempted to borrow from internet culture for your costume, remember that if you have to explain the story behind the costume for it to work, you're going to reveal how much time you actually spend on Twitter.

Costumes that are of the moment are great if they feel like they haven't been crowbarred in, or border on the offensive. Buying an orange feather boa from Etsy and going to your boss' drinks party as the California forest fire isn't a good idea. The same goes for dressing as Greta Thunberg, even if it is in support. She's a child, it's weird.

The most straightforward ideas are the best, as one member of the Esquire team demonstrated when he presented his costume for 2019: a t-shirt saying 'Flat Earthers Of The World Unite'. Chilling stuff indeed.

This story originally appeared on Minor edits have been made by the editors.

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Olivia Ovenden
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