Halloween Costumes for the Cutesy, Charming, and Cheeky Among Us

I need to see pics of Lowly Worm drunkenly kissing @dieworkwear.

If you know me, or just read this blog with any regularity, you know that I take costumes *very* seriously—check that link for more rationale as to my costume philosophy, tips on throwing a costume party, and an expansion pack of ideas to augment these! A few weeks ago, I realized I hadn’t for a while experienced my customary lightning bolt of an idea for a costume that typically splits my skull, Athena-like, at least a few times a month, and I got nervous that the well had dried up. But no, the Muse of costuming has graced me once again, and below are my latest ideas for solo, couples, and group costumes that are a) financially accessible b) comprised of largely useful/reusable elements and c) recognizable enough to be fun for all while unique enough to actually be fun. I’ve even included ideas for the perfect simple photo op for each costume. Walk with me.

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The cutesy

Solo: Lowly Worm

Looking at this worm lowers my blood pressure by 75% every time. I love the above pic, but proportionally it’s helpful to see him straightened out:

For this outfit, I’d pair a white button-down with a cornflower blue sweater and kelly green pants or a maxi skirt, finishing off with reddish sneakers and a similarly-colored bow tie (or a pussy bow of sorts fashioned from a silk ribbon or even a fabric scrap), plus a jaunty green cap adorned with a yellow bow. For more accuracy, the blue and green swaths should be approximately the same length, so a longer sweater or lower-waisted bottoms might be in order, but Lowly does exude the energy of someone who’d hike their trousers up to their armpits, so feel free to style as inspiration guides you. If you don’t think you’ll get future use out of a green brimmed cap, I think a baseball cap encircled by a little tasseled scarf or something similar would be just fine in the eyes of God and Lowly.

Photo op:

Steal somebody’s skateboard, stick your tongue out insouciantly, and transcend the sorrows of this broken world to truly capture the holiness of this skinny little thing!

Multi-person: Sonny Angels

Here’s an opportunity to re-up on your skin-toned base layers, just in time for colder weather: whether you make a biannual (meaning once every two years, as I do) Uniqlo trip or have invested in hardier thermals and shape wear (maybe even vintage?), this costume won’t require you to get your hands on much more than a few pieces that can then be worn into the ground, under sheer stuff or any old outfit that’s not quite warm enough. A skintight long sleeve and leggings, both as close to your skin tone as possible, would be enough, but depending on your plans and the weather, I think a camisole and bike shorts, or some combination of the above, would work perfectly. I personally am not going to be the one to suggest a sexy Sonny Angel costume because I’m sure there are more worthy cancellations in my future, but hey—I’m not a cop. I’m loathe to recommend Skims (and won’t link to its site), but I think that’s probably the most straightforward avenue to pull this off.

Of course, the headpiece will require a bit of craftiness (or perhaps commissioning someone craftier than you), but I’ve made a few costume masks and hats that, after the holiday, have hung on my walls like trophies for years to come, and entering a second life as decor is not tantamount to discarding something. I could see a knit bonnet being doable with a fairly tight turnaround! A sparse few animal headpieces are available on the official Sonny Angel site for $35 apiece, but a homemade hat would be so much more true to the precious ethos of the naked babies.

In a pinch, I don’t think it would be mailing it in to grab a (preferably shallow, not fold-over) beanie and matching plain scarf, strip of fabric, or stretchy headband to tie around the head old-fashioned toothache-style under the hat, then affixing a leaf or stem made of materials like wire, tinfoil, and fabric scraps to its apex—you could probably even do it without puncturing the beanie by pinching the tip and wrapping it with wire to create a little nub of a base. The fruits and veggies would definitely be easiest to pull off this way!

The cherry on top of this costume would be if you did the Angels’ minimal makeup routine, drawing three eyeliner lashes on each eye and rimming the waterline in white, plus adding a dollop of rosy blush to your cheeks—if I were doing this costume, I’d probably frustrate myself trying to do the glue stick eyebrow-hiding trick to draw on the tiny wisps of a brow seen on the Angels, but I won’t blame you if you don’t bother.

Photo op:

All the Angels peeking over a fence, wall, or the like with the same sanguine smirk.

The charming

Solo: Stuffed Olive

One of the best costumes represented as a costume in a movie. If you’ve never seen Angus, Thongs, and Perfect Snogging… well, you don’t need to, but if the damage was done 15 years ago and Aaron Taylor-Johnson’s wheezy “Geoooja” still brings a glint to your eye and a palpitation to your heart, this costume has been revolutionized by TikTok:

Yes, I believe they’re wearing huge green paper lanterns such as this $50 beauty, plus green tights and red turtlenecks and beanies. You could always go the orthodox papier mâché route, but I think minimizing grief and maximizing joy is what a more self-actualized, less ageist Georgia would tell you to do.

Photo op:

Have a group of your sexiest-dressed “friends” stare at you in disdain and pity.

Multi-person: Juno and Bleeker

I rewatched Juno with a friend who’d never seen it before—it was the first “inappropriate” film I was ever privy to, around age nine, and I am doomed for the rest of my life to never think anything is quite as romantic as singing a Kimya Dawson song with my beloved on a stoop. Also, I sat next to Elliot Page at a restaurant once while he was on a date and I had just come out to half of my family as transmasculine—it felt like an after school special—so I feel like he and I have a deep-seated connection. Anyway, I think Juno and Bleeker comprise one of the sweetest couples’ costumes that hits the right balance between nostalgically twee, comical, and romantic, and is super easy to pull off with clothes from your joint closets (plus a fake belly).

For Juno: essentially any combination of bootcut jeans + striped shirt + patterned hoodie + patterned sneakers—plaid or camo would be perfect. I don’t think any adherence to the movie’s exact costumes is required—an ad hoc situation with whatever layering you’re inspired to add (a button-up! a chore coat!) captures the spirit of the original diva as long as the striped tee and slightly flared denim are there to ground the fit. Little details, like matching the color of your shoelaces to the stripes on your shirt, would elevate this costume to transcendent, but probably only for your blessed self—everyone else is gonna be too busy rubbing your fake belly to care.

For Bleeker: this outfit is a little more prescriptive, but only three items are *really* necessary: a maroon t-shirt or sweatshirt (gold graphics optional), the shortest goldenrod running shorts money can buy, and a matching terrycloth sweatband. Coordinating tube socks is a huge boon to the look, and if you’re wearing short sleeves, terry wristbands would be the kicker, but no harm no foul if you’d rather not buy those essentially vestigial items. Literally any pair of running shoes will do to finish things off!

Photo op:

Pure romance is Juno flipping the camera off as she and Bleeker kiss—you MUST both be smiling as you smooch to make this work.

The cheeky

Solo: Derek Guy

This costume came to me in a midnight cold sweat, and is perfect for dandies or menswear nerds who wouldn’t deign to drop their standards of dress for a bawdy night out—the Napa leather belt stays ON during Halloween. If you don’t know of “Derek Guy,” or @dieworkwear, you can ignore this costume, but if you do, you’re probably already fostering a bead of sweat on the nape of your neck, mentally scouring your closet for what you could wear that could possibly live up to the man’s sartorial mythos. A cursory scan of his recent tweets yielded plenty of potential pathways for how to dress while carrying a makeshift mask (print out the above iconic avatar, double-sided, laminate, and either hole punch and tie it onto your face or glue to a popsicle stick or the like for a handheld option):

A chambray shirt under a Western-leaning gray suit;

A preppy, nautical look with a knit polo, white trousers, and tortoiseshell Wayfarers;

A Lemaire (or Uniqlo for Lemaire)-ish look that pays extra attention to the cut and drape of each piece…

…The possibilities are near-endless, and should certainly be comprised of either pieces you already own, or ones you wanted to buy anyway. Leftist politics and a quick wit are required.

Multi-person: Angelina and Billy Bob

Our last costume today is another couples’ option, this one significantly sexier—the heartbreakingly short-lived and retrospectively inexplicable Angelina Jolie and Billy Bob Thornton circa 2000. This one’s for the real lovers who aren’t afraid to be a little too much with it.

For Angie: black leather pants, a gray or light blue baby t-shirt, the iconic Billy Bob tattoo drawn onto the left shoulder, and though it’s not visible in this era-defining red carpet appearance, why not add a vial of your beloved’s blood around your neck on a chain? I’ll leave it up to you two to decide whether it’s real or faux (I know what I’d choose…).

For BB: brown leather pants, some stupid black trucker cap (these are so, so easy to find at any thrift store worth its salt), a button-up that looks like Alex Grey got drafted to make wallpaper for a mental institution (paisley works, too), a goatee (100% required, whether drawn-on or, if you’re enough of a WINNER to commit to this look, real), and a matching blood vial.

Photo op:

Get your most perverted friend to snap flash photos of a double-fisted fondling-plus-lip-bite maneuver. This is level S stuff that can only be accomplished by people who truly love each other, so this costume is a great test for three-month-old couples who want to make sure they can really see each other as fit for the long haul.

This was a delight to put together—I hope it gave you some ideas for now or later, and I SWEAR if you do one of these costumes and don’t send me pics here or on IG… I don’t know, you’ll probably be fine, but I’ll feel a mysterious pang of wrongness, and I’d like to avoid any more of those than necessary.

<3 ESK