Halloween-Costumes-Through-the-Years Montage

In honor of Halloween, these are the photos that exist. I do remember 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.

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 had seen Bugsy Malone. We were hooked. So we dressed up as flappers. Sadly, though, the neighborhood mothers, opening the doors to trick-or-treaters – all 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. 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 went as a blind mute French beggar. The sign around my neck says “J’ai faime!” (Quoi??)

My boyfriend didn’t wear a costume. Kidding.

He dressed as a nerd.

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


And here we are a couple hours, 2 makeout sessions, and many underage beers later.


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. They died within months of each other. Here are Jackie and Mitchell, channeling Jackie’s famous and beloved grandparents, Chester and Millie.


It is one of my favorite pictures of all time.

A year later, Mitchell and I dressed up as Andy Warhol and Edie Sedgwick.


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 a New Year’s Eve party? Maybe someone in line for the fallen Hapsburg throne would, but a regular Rhode Island girl? She’ll just spritz her bangs and put on a little black dress.

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.

Jackie said, upon seeing the photo again, “I look like the secretary at the Woonsocket DMV” – which is truly local humor. As far as I know, there is no Woonsocket DMV, but that doesn’t matter. She is completely right about what she looks like. A Rhode Islander would understand.

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 offensive. 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, even though it was Halloween, so everyone was in black suits and cocktail dresses and we show up looking like that. And our clothes weren’t costume-y enough to protect us, so that 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.

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, Al Capone guffawing with Jackie Kennedy.

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. 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 and devils. But 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 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 as Squeaky Fromme. No pictures exists of that costume, but I remember it fondly.

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25 Responses to Halloween-Costumes-Through-the-Years Montage

  1. Betsy says:

    Love it! Thank you!

  2. Sheila Welch says:

    Sheila, Thank you, thank you for this. This is so cool. I don’t know which one I like best, they are all so precious. Oh my goodness. So beautiful, funny, memorable.
    Thank you.

  3. sheila says:

    Sheila – thank you, I’m so glad I have them all. I am sorry that my Squeaky Fromme was not immortalized. I wore a black cape and had an X drawn on my forehead and carried a huge sign with Charles Manson’s face on it. Yeah, I was really popular that night.

  4. tracey says:

    Oh, I love it when you post these! I can never decide which is my favorite. They’re all so brilliant in their own ways. Your cheekbones are to die for, my dear.

    But this is killing me:

    /And I was insane enough to be carrying around a fake doll./

    And also to be bottle feeding your doll.

    I would have killed to be a fly on the wall at that party, watching and listening to all the dressed-up people sizing you two up. Hahahahahaha. Your face in that photo is hysterical to me.

    What are all the orangey pom-pomy thingies on your baby doll there, Mia? Is it just rife with pom poms??

  5. tracey says:

    Also, your pregnant belly is like a stack of books. Wha??? Hahahahahaha.

  6. sheila says:

    Tracey – hahahaha My original idea had been to somehow Velcro a BUNCH of baby dolls all over my body. Which is insanely hostile when you think about the real-life situation. I settled for one – which just made it all the more weird when we showed up at the formal-dress party. You throw a party on Halloween and it’s NOT a costume party?? You could have given us a heads up. We sipped our cocktails in our ridiculous shlubby clothes and snuck out of there as soon as we could.

    Look at how busted and guilty Mitchell looks.

    It still cracks me up.

    Yes, I like to have my Halloween costume represent a real-life person’s real-life tragedy!

  7. sheila says:

    hahaha Yes, a lumpy fake belly. I can’t remember what I put in there. So wrong. I’ve blocked it out.

  8. sheila says:

    My smile is completely demonic in that shot where we are dancing. I’m almost embarrassed looking at it.

  9. sheila says:

    I remember specifically our friend Maria who was taking that picture of us as Woody and Mia, started in closeup – and then murmured to herself, “Oh wait, have to get the shoes.” Because look at Mitchell’s shoes.

    Good work, Maria.

  10. tracey says:

    Hahahahahahaha! The shoes! And Mitchell’s eyes are so huge, they almost fill the glasses frames.

    Your expression in that photo — I don’t even have words to describe it. You look so wary and protective and kinda pissed like, “Can’t you SEE?? I am TRYING to feed my baby.”

    Your Mia outfit is so spot on. The skirt!

    Yes, no Elvira or Wonder Woman for you. Sharon Tate, Mia Farrow. Hahahahahaha.

    I do love your little blonde witch in her handmade Irish sweater. So so cute. Brendan’s face is cracking me UP. He’s a ghost who looks like he’s seen a ghost!

  11. sheila says:

    He seriously has no idea what is going on and why he is in that costume and it just makes me laugh so hard!!!!

  12. Ann Marie says:

    I like that witch carried a purse. As you do.

    At least I *think* it’s a purse?

  13. sheila says:

    Yes, it looks like a big straw ladies’ purse with one of those hard clasps. I have no idea what is going on in the picture. Yet again, my brother and I look like charity cases in Belfast, circa 1973.

  14. Kate P says:

    Wow–what a chronology of costumes. Creative ones, too!

    The whole flappers story just blew my mind. Especially seeing that a turtleneck was part of your costume! That must be a special class of hooker.

  15. Maybe it’s those giant red sunglasses. Anyways, my inner Tex Avery wolf is howling.

  16. sheila says:

    Kate – Or a chilly hooker.

  17. sheila says:

    Peter – Thank you?? hahahaha We all should have an inner Tex Avery wolf.

  18. sheila says:

    Sadly, you can really see my lazy eye in that last photo. Maybe only I’m aware of it, but that’s all I can see when I look at that picture. “Hey, look at my lazy eye!”

    I love those sunglasses. I bought them for 2 dollars at a stupid shop on Canal Street.

  19. Maureen says:

    I love these pictures! I agree with tracey, you have amazing cheekbones!!

    I am also in love with the tea kettle in the first picture-adorable.

    Happy Halloween!

  20. Kathy says:

    Enjoying your memories of past joys and insanities… trying to remember if I had any clever costumes in my past (I don’t, sadly)… just memories of rainy Halloweens (live near Seattle) and not using paper bags to Trick or Treat because the rain melted them… used pillow cases (large and waterproof) … when I suddenly realized that my Trick or Treat days PRE-DATE PLASTIC BAGS. OMG. I’m sharing this as a gift to you and all of your fans, who are thinking about their good old days and feeling old. Could be worse. Happy Halloween!

    • sheila says:

      Kathy – ha! Pillow cases are a good solution! More room for candy, too!

      Last night, I went out trick or treating with my nieces and nephew – it was a tiny bit drizzly (right on the ocean) but it was chilly, misty and beautiful. I never get trick or treaters in my apartment building in New Jersey – so it was so fun to go out with my family!

      Hope you had a good one!

  21. Ryan Cox says:

    What now seems like many years ago, back when my friends and I were all in our 20’s, before everybody had kids, we used to have fun themed Halloween parties. The best was our Dead Celebrities party, where everyone had to dress like a dead celebrity, and incorporate how they died into the costume. I went as Sal Mineo with a large, bloody gash in my chest. Talk about tasteless. I also have no defense.

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