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The Dumbest Halloween Costumes of All Time

Hey, there's a "best" in "dumbest!"

Em Seely-Katz's avatar
Em Seely-Katz
Oct 01, 2025
∙ Paid
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Hi all, no way around it, I have already sunk deep into the hopelessness that, for me, accompanies seasonal depression but in this case is exacerbated by having a boss who hates me for literally no reason and barely enough money to cover groceries (forget seeing John Waters at the theater down the street from my house in December…). It sounds so simple but right now, in my mind, it’s all insurmountably bad and I am teetering on the edge of a deep pit of despair. The one good thing about this misery is that it elicits the stupidest ideas of all time in regards to Halloween costumes—don’t ask me how that works, but it’s science, baby! Enjoy my brain vomit below and please consider becoming a paid subscriber for only $1.50 a month or $15 a year using this link so I can buy a stupid pumpkin or something from Trader Joe’s for safe, constructive knife-based stress relief. Love you guys, thanks for being here even on my worst days. Also, please excuse any typos—I’m down bad, after all!

If you like these posts, please let me know by liking and commenting here or on Esque’s Instagram, subbing to the Esque Substack (this) for free, getting bonus posts for five bucks a month, or for ZERO DOLLARS, share (tag me if on IG so I can see and thank you)! If you share with three friends (or enemies), you’ll automatically get a free month’s subscription to Esque’s paywalled posts. If you buy anything from an Esque link, there’s a chance I’ll earn a percentage commission at no cost to you—if you end up inspired by anything below, please send over a photo of your new togs by replying to this email and I’ll comp you a month of Esque!

If you cannot afford the $5/month, I totally understand—respond to any of my email sends and I will get you a $1.50 subscription or comp you, whatever you need. Esque is for everyone!

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THANK YOU for being here, and I am always available @that.esque on Instagram for sartorial scandals/situations/summons. Here is a little preview of what’s below the paywall:

Sellout Segment

Before we begin the main event, I have decided that I’m going to try and include a few items every week that I either genuinely want or recently purchased with my own $$ in an effort to be more consistent with my affiliate links without being a total monster and compromising the quality of my blog, most of which is, as you know, centered around more abstract content and secondhand or DIY buys. I will always provide rationale for my recs and they will never be behind a paywall—even just clicking them helps me in my efforts to start getting free stuff from companies I’ve been giving free PR to for going on 5 years now, so your attention is much appreciated (and the stuff I’m including is actually cool and/or useful—no $890 fuckass jelly flats here, thanks)!

Vivaia Miley Flats - $139

The lovely

Sarah Isenberg
recommended these to me when I was looking for non-ugly shoes I could still conceivably wear to work, and I have since done so and can confirm that even for someone with glass bones and paper skin like myself, they are viable choices for an eight-hour workday, though I will say that the laces above come untied at the drop of a hat. However, the shoes come with two other pairs of cute laces that are much less prone to untying themselves in gingham and polka-dot, and I’m excited to try them both. Here they are in sunnier times:

And here’s my genius copywrited idea to get satiny black ribbon and string a red pom-pom on each for a Pierrot-core twist:

What do you think?

Dedcool kindly sent me some stuff for a piece I’m working on about Hispanic-founded fragrance brands—I got the new Mochi Milk EDP, the Taunt body lotion, and the Discovery Set.

My surprise favorites were the Sunlit Blooms EDP from the Discovery Set, which is more than the sum of its notes—the salt makes the orange blossom pop in a surprisingly fruity fashion; and the Taunt body lotion which smells like a lotion from my childhood so strongly that it made me emotional upon first sniff. Overall, I was very impressed! More to come about this soon.

Lastly, I did get sucked into the Molly Goddard x Baggu collaboration, but I had never owned a Baggu before so I felt less weird about owning these than I would if I had a grotesquely large collection as you see so frequently on TikTok. The Ruffle Shoulder Bag is spacious but not bulky, and my boyfriend told me it looks like a slutty little skirt-turned-purse, which I like. The recycled ripstop tones down the girliness a bit, as does the full-black colorway, and I feel so much more put together carrying this than I did with any of my old ratty tote bags, though it functions identically. The quality seems unimpeachable so far, and I jostle my bags around like nobody’s business on a moment-to-moment basis.

My real saving grace, though, has been these Go Bags, which turn the gaping maw of the purse into a blessedly categorized chasm in which finding anything from my earbuds to my eye drops is now no longer a matter of blindly feeling my way around the crumby corners of a seemingly endless array of tchotchkes and trash. Papa, anm I a real boy now?

Anyway, onto the costumes!

This first one, I must admit, was not my brainchild—I give all credit to

Eleonor Botoman
, who at least a year ago planted this cursed seed in my mind. Don’t you see it? It’s so simple, and yet, so beautiful: a white top of your choice, a piece of silver duct tape, and either a eyeliner-scrawled message across your cheek and hand OR an official temporary tattoo from the lads over at No H8. They come in five packs for $6. This is the easiest, and possibly both the funniest and most melancholic (given our current circumstances) costume you could possibly impress with, costs next to nothing, and gives you an excuse not to talk to anyone you don’t want to at your next Halloween bash.

The variations on this costume are endless, just look up “No H8 Celebrities” for a trove of inspiration. I like this Jane Lynch iteration, which leads neatly into my next horrific idea…

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