Halloween Costumes Through the Years

In honor of Halloween, these are the photos that exist. There were other costumes but I lack evidence.

The first Halloween costume in the recorded history of my life shows me as a witch with a bright blonde plastic wig. The witch is also wearing an Irish knit sweater, probably made by mother. My brother is a confused ghost who is also wearing an Irish knit sweater.

All childhood photos of me and my siblings look like some heart-tugging ad for a Belfast Catholic charity in 1974.

Here’s a photo of my brother and me a couple years later. I am a bunny rabbit. He, obviously, is a clown. The height of his hat is taller than his actual body. My mother made both of those costumes.

Here I am as a flapper. This is during my junior high years, my Eight is Enough pariah years. My best friend and I were obsessed with the 1920s. We loved flappers. We had seen Bugsy Malone. We loved the entire decade. So we dressed as flappers. Sadly, though, the neighborhood mothers, opening the doors to trick-or-treaters – assumed that we were hookers. I remember one woman saying, “Oh, here are two ladies of the night” and I didn’t even know what she was talking about. I didn’t know what that phrase meant. I think it’s PERFECTLY obvious that I am a flapper! This was my last year trick-or-treating.

Now we move on to college, when it becomes cool to dress up again. Here I am at a party with my college boyfriend. I was a blind mute French beggar. The sign around my neck says “J’ai faime!” Sheila: Why? or … Quoi?

My boyfriend didn’t wear a costume. JUST KIDDING.

He dressed as a nerd.

Here we are at the start of the party, costumes intact, the illusion complete.

And here we are a couple hours, 2 makeout sessions, and many underage beers later. He is clearly telling me something very important.

We were just about to play Anne Shirley and Gilbert Blythe in our college production of Anne of Green Gables. This is Anne and Gilbert, Behind the Music.

At that same party, my friends Jackie and Mitchell dressed up as Jackie’s grandparents, who were famous to all of us. Chester and Millie. It was like one word. Chester and Millie, Chester and Millie. They died within months of each other. Here are Jackie and Mitchell, channeling Jackie’s famous grandparents, Chester and Millie.

This is one of my favorite pictures of all time. Look at Mitchell’s eyes! He is completely in character. I am also particularly amused by Jackie’s mouth. What is Millie saying to Chester? Is she calming him down? I hope so, cause he looks a little worried.

A year later, Mitchell and I joined forces and dressed up as Andy Warhol and Edie Sedgwick. The expression on Mitchell’s face in this photo kills me. He looks so bored, so arrogant, so over it.

Two of my friends in college were bridesmaids in a wedding and were forced to wear puffy royal blue gowns … and of course the bride said, “You’ll wear them again – maybe to a New Year’s Eve party!” What kind of person would wear a puffy royal blue gown to New Year’s Eve? Maybe someone in line for the fallen Hapsburg throne, but a regular Rhode Island girl? She’ll just spritz her bangs and put on a little black dress with shiny black heels.

Anyway, the dresses were infamous, and the bridesmaids went about in a state of fury about them, and Jackie, who was one of the unfortunate bridesmaids, would sometimes put the dress on and come down the stairs, singing “Hit the Road, Jack” as though she were a pathetic over-the-hill lounge singer. We’d all be hanging out downstairs, Jackie would be dressed like a normal person, then she would disappear … and before we realized she was gone, back she would come, singing some cheeseball song, wearing her royal blue bridesmaid gown.

So that Halloween there was a huge bash at the house of some friends in Eastward Look, down by Scarborough Beach. A big party house. Jackie and I decided to go as the Sweeney Sisters (who were huge at the time). We both wore the royal blue bridesmaid gowns and false eyelashes. As much as we could, we tried to stay in character. We burst into the party singing “Clang Clang Clang Went the Trolley” and just took it from there.

At the end of the night, the entire party went down the end of the road to the beach and stood on the sand, shivering, holding beers, singing and laughing. Jackie and I were still in our gowns. We must have looked insane. But it was Halloween we could get away with it.

Jackie said, upon seeing the photo again, “I look like the secretary at the Woonsocket DMV” – which, I suppose, is truly LOCAL humor. There is no Woonsocket DMV, but that doesn’t matter. It’s the ENERGY she’s talking about … and she is right ON. She looks totally like the secretary at the Woonsocket DMV.

So yes, indeed, the dresses were “worn again” although perhaps not in the fashion that the bride intended.

A couple years after that – while we were living in Chicago – Mitchell and I got invited to a Halloween party. The whole Woody Allen-Soon Yi thing had just exploded, so we dressed up as Woody Allen and Mia Farrow. Please note that:

1. Mitchell is carrying Crime and Punishment
2. He is using photos of Geisha girls as a bookmark

So wrong. So funny.

The weirdest thing about it was that when we arrived at the party, NOBODY ELSE WAS IN COSTUME. We had somehow missed the memo that it was a “formal” party – so everyone’s in black suits and cocktail dresses and we show up looking like that. They weren’t even enough of a COSTUME to protect us. It just appeared that we were slobs who didn’t know how to go out in public. And I was insane enough to be carrying around a fake doll.

Then, one year, I was invited to a Halloween party where we had to dress up as someone who was actually dead. A person from history. At the party, I would look around and see Jesus chatting with Endira Gandhi chatting with Edgar Allan Poe.

I went as Sharon Tate.

I have no defense.

I have written “Helter Skelter” all over my arms and legs with red marker.

To make matters even more evil, I rode the subway to the party dressed like that. I had a huge pregnant belly as well. I got on the F train from Brooklyn, took it to 47th Street, and then walked through the crowds to the apartment where the party was which was on the east side. I was freezing. Now, it was Halloween night, so I certainly was not the only one in costume. I saw witches and warlocks and Playboy bunnies and Medusae and a couple of Chuckies and Buzz Lightyears. I sat on the subway surrounded by daemons from the deep. But there was something different about my costume. I was a walking crime scene. People looked at me once, grimaced and looked away, before glancing back to see if I really was who I seemed to be.

OR, even better, they just stared at me, shaking their head slowly in judgment and disapproval.

Here’s the side view of my pregnant belly as I dance with Jackie Kennedy and Mrs. Al Capone.

A couple of years earlier, along the same lines, I had gone to a Halloween party in San Francisco as Squeaky Fromme. Some bitch at the party took one look at me and said, “You know, that’s not funny.” Never said it was. No pictures exist of that costume, but I still remember it fondly.

Last year I didn’t dress up at all. Well, not really.

It’s also my dear nephew Cashel’s birthday. Happy birthday, Cashel!