The Halloween Costumes That Still Haunt Us: Three True Stories

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When it comes to the photographic record, Halloween must have the highest risk/reward ratio. A daring costume brings with it dreams of glory — and the risk of impossibly humiliating failure. As we prepare for this year's masquerade, the staff of the Cut remembers the humiliations of yore, from an inappropriately sexualized toddler to an accidentally race-baiting 11-year-old.

Feast your Schadenfreude on the awkward tales of fashion staffers Sally and Amelia, and photo editor Emily. Got a worse story? Commiserate in the comments.

Sally Holmes: I Dressed Myself As an Asian Child

When I was about 11 years old I dressed up as an Asian [fill in the blank] for Halloween. I’ve always had an affinity for Asian things: Asian food, Asian babies, and my best friend is half Chinese. The summer before I turned 11, my mother visited Hong Kong and came back enthusing about the city, the sights, and the food. Real Chinese food, I learned with fascination, came to diners on little carts that traveled from table to table carrying different dishes, a phenomenon I would later come to know as dim sum.

The gifts my mother brought back for me included a wooden comb covered with delicate painted flowers and an embroidered red silk shirt and pants set. Apparently I was very eager to wear my new getup and the first opportunity presented itself at Halloween. Arriving at a friend's house to trick-or-treat, I put on my red suit, dabbed my face with baby powder, and I think I even brushed my hair with my new wooden comb. Then I joined the other kids — in their culturally appropriate devil, angel, and witch outfits — and went door to door. I have no memory of the reactions my costume elicited, nor of what I said or thought I was. Asian something. Was I a little geisha? I don’t think I knew what that was, or that geishas are not Chinese but Japanese. Mulan? This was before that movie came out, and in any case I did not look like a cross-dressing warrior.

I suspect I told people I was an Asian child. And what an Asian child I would have been: Always tall for my age, I must have had a good few inches of ankle exposed, plus my face covered in baby powder. The baby powder. I hope I told people I just wanted to wear the red silk suit because it was a costume my mother gave me and I thought it was pretty. But I know I didn't. Thankfully, my parents have no pictures from the night. I’m sure my friend does, though, and it will someday return to haunt me. But for the moment, with no visual record, I can sit back in peace and just think WHY?

Amelia Diamond: My Mean Girls Slutoween Moment

Aesthetically speaking, sixth grade was a difficult year for me. I had eyebrows I wasn't allowed to pluck, my hair cut like Olivier Zahm's, ears that stuck out like teacup handles, and braces with rubber bands that I'd color-coordinate for each holiday — red and green for Christmas, pink and white for Valentine's Day. And I had a weird sense of humor.

At my middle school, orange-and-black braces season culminated in a costume dance. It was to be my first real DANCE, the kind with boys lined up on one side and girls on the other. For the big event my friends and I thought it would be hilarious to go as the Marx brothers, so naturally I chose the one that would require a fake nose: Groucho Marx, slapstick thirties comedian loved only by grandparents and 11-year-old weirdos.

Yes, I had decided to go to my first real boy-girl dance dressed as a man.

I remember strutting in, ready to take on the night in black-rimmed novelty glasses with an attached giant nose, mustache, and bushy black eyebrows. I borrowed a shirt and tie from my father, and planned to impress everyone with dance moves copied from TRL and practiced in the bathroom mirror. I remember thinking: This is gonna be awesome.

It was not awesome. It was like the scene in Mean Girls when LiLo walks into a Slutoween party dressed as a zombie bride. Yes, we were only in sixth grade, but we were city kids and at our first boy-girl dance. The result was like a sexy pet store, with glossy-lipped bunnies, birds, and kittens roaming around the school. Naturally, I tried to rectify the situation by removing my fake nose and knotting my white button down into a belly shirt. Midriffs weren't allowed at our school, though, so I had to undo it.

If memory serves this didn’t actually ruin my night — I just hung out with my equally awkward friends and ate more candy than I would have been allowed at home. For guilt purposes, however, I include descriptions of me Charlie Browning around like George Michael in Arrested Development when I retell the story to my parents.

Emily Shornick: Inappropriately Sexy Toddler Tableaux

It was the summer of 1989. My family had recently moved from middle-class Queens to an affluent Connecticut suburb. My brother Zack and I posed in our new backyard, me in a bikini and he shirtless and in coke glasses. With the reverence of Moses on the mount, Zack raised a book over his head. The Intimate Sex Lives of Famous People, it said, in case my sultry pose didn't get the S-E-X message across. An uncle — who, despite the mustache, I swear is not a creep — looked on.

I have a hard time understanding why my mother, a marketing executive who burned her bra in the seventies, would delight in sexualizing her 3-year-old daughter in an incestuous tableaux. I am most horrified by the overt markers of childhood — my brother’s Velcro shoe in the background, a Donald Duck Band-Aid on his knee, and my exposed, tiny nipple reminding the viewer that I was too young to fill out a halter bikini.

The only justification I can muster —and I am stretching here for you, mom and dad — is that this sexualization is intertwined with an earnest interpretation of eighties greed culture. There are Hollywood-inspired palm trees on my shorts; sex and fame are held above all else, an offering to the yuppie gods in gratitude for our new one-acre property. But no matter how many times I watch Wall Street on cable, and no matter how many Sally Mann photographs I defended in art school, I cannot look at this picture and not want to puke a little.