What Was Your First (Or Favorite) Halloween Costume?

What Was Your First (Or Favorite) Halloween Costume?

What are you going as for Halloween? As that’s the question so many people are asking right now, I thought it’d be fun to revisit the costumes of Halloweens past. So I asked a group of writers at various fashion-slanted blogs and magazines to share their first — or favorite — Halloween costumes. Here’s what we got (some with bonus pictures!!!).

Leah Chernikoff, executive editor of Fashionista

My favorite Halloween costume was actually pretty recent. My sister lives in New Orleans where they do everything big so a few years ago we went all out to be the creepy twins from The Shining. We wore blood-stained matching Land’s End school uniforms and held hands and shouted “red rum” at drunk people.

Charlotte Cowles, senior editor of The Cut

Before I hit my late teens and Halloween became an excuse to wear the sluttiest outfit I could possibly muster, my mom made majority of my Halloween costumes on her sewing machine. This was so sweet and maternal of her, and I was totally ungrateful and just wanted one of those store-bought Disney costumes. (My best friend in second grade, Julie, had this gorgeous yellow dress that Belle wears in Beauty and the Beast and I was sickeningly jealous.) Anyway, there was one exception: When I was six, my mom made me a truly kick-ass mermaid costume that featured a lovely tail made of green silk. She stuffed it with filling so that it was like a big fin-shaped pillow, and sewed it to a long green skirt so that it flopped around when I walked. For obvious reasons, that was my favorite Halloween costume.

Kerry Folan, editor of Racked

Thirty years later, I still wonder what private joke my very sweet, very Catholic mother was making with herself when she sewed me into a devil costume for my first Halloween.

The neighborhood I grew up in was unpretentious, middle class, and above all, parochial: An imposing Catholic church sat square in the middle of the well-kept Colonial houses, its elegant steeple rising above everything else in sight. As we got older, my brother and I would run loose after school in our disheveled plaid uniforms with the other neighborhood kids — nearly all of whom attended the Catholic grade school around the corner from our house — and be called home for dinner at 6:00 each evening by the church’s punctual Angelus bells.

As the center of the community, the church very naturally steered the Halloween activities, too. In the afternoon, the little kids paraded around the field in all their costumed glory. Later on, trick-or-treating dads with cans of Budweiser in hand would lead their disguised progeny along the short-cuts across the church grounds (in our neighborhood, children received candy while their parents received roadies). And later still, the older kids would gather in the parking lot to do everything teenagers always do on Halloween. In a word, there was no way to ignore God on All Saints Day, or any other day, if you lived there.

So I like to imagine my mom smiling to herself as she stitched the tiny red costume — complete with trident and devils’ horns — for her two-year-old daughter. Perhaps she already knew that her children would learn to exercise the outer limits of her patience, and that she would answer every test over all those years with ecclesiastical kindness.

Tavi Gavinson, editor-in-chief of Rookie

One of my first Halloween costumes was a teacher at age four. I wore blue zig zag-printed pants, like all educators do, and collected candy in a tote bag my mom had that said “TEACHER STUFF” on it. FUN! At an age where I could’ve dressed like a FAIRY and sincerely believed I was one, I for some reason thought dressing like I had my dad’s job would be just a blast.

Heather & Jessica, Fug Girls

Jessica: My first Halloween costume (that I can completely remember) was a fairy princess. I must have been three or four, and my Grandma made it for me — she made a lot of my Halloween costumes, because she’s pretty crafty. My dress was pink, and obviously I had a magical wand and a crown, both of which were covered in little paste jewels and had ribbons all over them. I MAY have worn my crown for several months thereafter, just with my usual ensembles. As everyone knows, accessories really do make the outfit.

Heather: I suspect my first one was the Sunmaid Raisin girl when I was three or four, and as an adult I am fond of the year I went as Karl Lagerfeld, but my very favorite as a kid was Annie — I had a red curly wig relatively like hers, and although it killed me that I didn’t have the EXACT red dress nor the EXACT black patent buckle shoes that went around the ankle, I did my best to substitute. I loved it so much, I don’t even know if it entirely counts as a Halloween costume, because I was prone to wearing it on random Tuesdays and such.

Laurie Henzel, publisher of Bust

I love Halloween so much, and for a few years in the 80s, my gay boyfriend and I went as famous couples, (Sonny and Cher, Nico and Brian Jones etc.) but I think my favorite was Salvador Dali and his wife Gala. I wore a glamorous gown and fashioned a hat with a giant lobster on it; he did a tux, cane and crazy moustache. I love doing historical characters because you can research fun facts and incorporate them into the night.

David Hershkovits, founder and editor of Paper

When I went as Barack Obama in 2008 and got all these funny looks from people on the street.

Kristian Laliberte, senior editor of Refinery29

There was a point and time when I actually purchased an Ed Hardy trucker hat and True Religion jeans. And, actually wore both of them. Non-ironically. A year later, in the heart of Christian Audigier-dom, I looked back and realized my egregious sartorial mistake. To atone, my Halloween costume addressed those sins and I went as Last Year. I piled on all the gnarly Ed Hardy, True Religion, Affliction (even a rabbit-fur lined Juicy Couture sweatshirt), shit I could find…and got spray-tanned. I guess I could use it again and go as “Jersey Shore.”

Jessica Misener, senior editor of The Huffington Post Style

When I was in first grade, my mom, who’s an avid sewer, made my sister and I unicorn costumes for Halloween. They were full-on jumpsuits made of shiny lilac satin, complete with mane and a unicorn horn stuffed with fiberfill. We made skits based around our unicorn characters and it was the bomb diggity. Actually, I wonder if I still have mine.

Tracie Egan Morrissey, senior writer at Jezebel

When I was in eighth grade I dressed as a pregnant nun. I wore the costume to my Catholic school, but I didn’t get in trouble, I think because that would’ve required an uncomfortable conversation about sex. Instead, they told me to remove the pillow from my stomach, so my costume morphed to “teacher.”

Anna North, senior editor of BuzzFeed Shift

When I was in grad school I decided to go as Robin Hood, and it turned out one of my classmates was a hunter, so I ended up driving way out into the woods to borrow a real bow from him. He also cut me off a tree branch that I used as an arrow. I was really proud of myself because I felt like I’d been on a quest, like I was going to actually become some kind of woodland hero.

Maureen O’Connor, senior editor of The Cut

My first Halloween costume was a brown paper grocery bag, which my mother cut three holes into, for my head and arms. We drew a clown outfit onto it, and she painted my face with a lipstick.

Amy Odell, editor of BuzzFeed Shift

My favorite was Daft Punk. I went with a friend and think I took the gold helmet. I guess the fact that I don’t remember is a sign it was an awesome time.

Jenna Sauers, writer at Jezebel

Halloween is not really celebrated in the country where I grew up, New Zealand. I remember once around age 12 some friends and I got dressed up — I don’t remember as what, but we were probably pretty half-assed — and tried to trick-or-treat in our Christchurch neighborhood. It didn’t work; most people were confused by this group of oddly dressed middle schoolers on their doorstep asking for lollies. One elderly man wouldn’t even come to the door. We went home and watched the original Halloween movie and scared ourselves half to death instead. So I don’t really have a concept of Halloween that predates my move to the U.S. when I was 18. I started to get really into Halloween when I realized it’s a great idea for a holiday: an almost totally secular opportunity for play and temporary self-transformation, with lots of drinking.

I’m very particular about my costumes. I believe in making my own — I never buy pre-made — and I do not believe in going as anything “sexy.” My favorite costume so far is probably the one I wore in 2009. I went as a Reverse Mermaid — you know, René Magritte’s painting of a fish with the legs of a woman, or a woman with the head of a fish. I spent really too much money (for just a costume) on a couple yards of silver, blue, and green stretch lamé at a poky little store on W. 39th St. First, I used some leftover curtain tape to make a kind of harness that went over my shoulders. Into the pockets of the curtain tape, I inserted the tape-wrapped ends of two bent wire hangers that together formed a pointed frame over my head. Then I made a pattern and sewed a stretch lamé fish head — sort of a giant hoodie with a misshapen hood part that would fit over my frame, with a hole for my face. I then cut hundreds of semi-circular scales out of the rest of the stretch lamé. I sewed the scales to the hoodie in rows, staggering them like roof tiles and working from the bottom up to cover my stitches. Lastly, I made puffy, three-dimensional fish lips that went around the face opening in the head and puffy little fish eyes (two circles of leftover black suede from an old thrift-store skirt I’d been cannibalizing were just right for the pupils). Underneath the arms I attached cheap green chiffon, ridged with radial pin-tucks to suggest fins. Add control-top nude hose and boy shorts and we’re done. It was a really great night. I went out to a total shit-show of a warehouse party in Williamsburg and was right up front for Bad Brains. Later, Brooklyn Vegan took my picture without my noticing while I was eating a falafel at 4 a.m. I was pretty proud of that costume. I don’t believe in recycling Halloween costumes, so I’ll probably never wear it again, but it’s still in my cupboard, harness, wire frame, deformed fish-head hoodie and all.

Molly Simms, senior editor of Bust

As a kid, I dressed as The Devil and Dracula several times, but one of my favorite costumes was circa my mid-20s, when I went as Wendy (from Wendy’s). I painted the corporate logo onto a huge piece of posterboard, and stuck my head through the circle; only her head is visible in the image, so I just wore pants and Converse. I was super comfortable, and I only partially destroyed the posterboard by the end of the night (with a combination of booze and out-of-control dancing).

Dodai Stewart, deputy editor of Jezebel

My first was Princess Leia. But my favorite, the one I did for like ten consecutive years, is Dorothy. I have homemade ruby slippers, which trail glitter all over the city, and a gingham dress someone made for me. My favorite on another person is when my sister, in fourth grade, went as a lab rat. She had adorable ears and whiskers and then syringes and bloody bandages hanging from her costume, which I think was long johns.

Kat Stoeffel, associate editor of The Cut

The first Halloween costume that I remember asking for was a unicorn. It’s weird to me, in retrospect, that a childhood interest in unicorns would translate into the desire to be a unicorn, and I guess for that I blame the very trippy 1982 animated film The Last Unicorn, in which a unicorn turns into a princess and, I think, back again. Asked how she constructed a child-size hood with a freestanding horn, my overachieving mother says, “Trial and lots of error!”

Dana Thomas, fashion writer and author of Deluxe: How Luxury Lost Its Luster

When I was six, my mother made me a costume to be Little Bo Peep: long skirt, bonnet (I already had a peasant-style blouse, this being about 1970). As it happened, we were in Miami because my father had a convention at the Fontainebleau, and I didn’t have a shepherd’s cane with me to complete the costume. So my mother took one of my Dad’s golf club irons — the humor in that being my Dad had bought and dragged golf clubs to Miami though he had no idea how to play — and tied a big pink bow around it, and that was my cane. I went to the party with all the other convention kids in a big, cool suite of the hotel, ate huge cheeseburgers from room service, watched Disney’s Babes in Toyland, and then the organizers gave out costume awards. I won Most Original, because of my nine iron with the big pink bow. The prize: a Mickey Mouse watch.

Verena von Pfetten, editor-in-chief of Styleite

My brain appears to have blacked out any early memories of my first Halloween costume. (My mother is many things, but a seamstress she is not, so at an age when homemade costumes ruled the scene, I probably wore a lot of garbage bags and miscellaneous hats.) But my favorite costume was also my first foray into that hormonal bastardization of Halloween, wherein the goal of the night is apparently to make oneself as creatively attractive as possible to those around you. My friend and I had decided that it would be great fun to dress up as Thing 1 and Thing 2 this year — “Such comfort! Such joy!”, we naively thought. We wore matching red sweatsuits, dyed our hair blue, and teased it sky-high. We were proud (and comfortable) in our leisurely ensemble until we saw another pair of Thing 1 Thing 2s — these wearing tight red mini dresses, bobbed blue wigs, and teetering precariously in stiletto heels. I later walked in on them having a threesome in one of the party’s darkened bedrooms.

Connie Wang, global editor of Refinery29

The best part about being Dr. Zizmor’s before-and-after patient was making the zits out of the Elmer’s glue and popping them later during the party for entertainment. They actually squirted white goo, which was pretty awesome. I cut some old sweats in half and glued them on top of these tie-dyed party and and black camisole (the ‘after’ patient’s I-now-have-confidence look), and made my boyfriend dress up as the doctor himself, complete with rainbow headband. The only downside was that all that fake pimple makeup wasn’t the best thing for my face, and I actually broke out in real-life zits the night after.

Related: Super Sexy Women’s Halloween Costumes

Nadia Chaudhury has graduated from dressing up as a princess because party dresses were easy to dressing up as Tami Taylor (with her Coach). Connie Wang costume photo by Maayan Zilberman.