The Worst Halloween Costumes I’ve Ever Worn

I have a complicated relationship with Halloween. I like pop culture and proving to other people how much better I am at liking pop culture than they are (which is what Halloween IS FOR, thank you very much), but I'm lazy. I'm so lazy. I'm lazy to the point that I seriously still consider dressing as "Three Hole Punch Jim" from The Office every year before accepting that I'd rather just spend the night making Christmas treats. (Which I did in 2011, and honestly? I have no regrets. Also, I ate them all that weekend — they were prototypes.)

This is why many of my costumes have been bona fide disasters. And not just in the "Aw, you tried!" sense of the word: I mean one time somebody asked what I was and I said I didn't know. Because I didn't. (I just put on a hoodie and, well . . . the rest you'll read about.)

So let's laugh at my misguided attempts at cultural relevence. Let's laugh at me thinking a hat made me Pamela Anderson. Let's recoil in shame at the hoodie story I just told you. Let's forget I ever went as a "sexy cat."

1. Al Borland (1996)
I'm just kidding: this costume was fucking sweet. Why? Hello, I looked like Al Borland. Like, from the hit TV show, Home Improvement. And I mean, I REALLY looked like Al Borland: my Mom painted a beard on me, I wore a flannel shirt from Northern Getaway tucked into my jeans ALSO from Northern Getaway, I made a homemade Tool Time hat, and I repeatedly said, "I don't think so, Tim." (And duh: I didn't think so, Tim.) Obviously, this costume has no business being in this round-up, but I'm obsessed with it, so if I don't bring it up once a year, I've failed the 11-year-old who went on a Halloween-themed figure skating trip with her class while dressed like a 30-something-year-old man who lives with his mom. (And honestly, good for him, he was trying his best.)

2. A present (1997)
When I was eight (1993), I went as a Christmas present for Halloween and it was ADORABLE. I was tiny, and I was walking around in an enormous cardboard box, and I looked like a goddamn holiday delight. Then, when I was 12 . . . or 11? (TOO OLD is the answer.) I tried to rekindle the magic. The problem? I looked 11 or 12. I was the height I am now. (5'7") I had a mushroom cut. I was wearing velcro shoes and a maroon windbreaker. (Yes, MAROON, not burgundy — there's a difference.) And I got chased around the schoolyard from grade fives trying to unwrap me. They didn't — but Christmas now is a little darker for me.

3. A "Spice Girl" (1998)
I am using quotes here because I wore my hair in pigtails and wore a short skirt then walked around the neighbourhood with my little cousin and her dad who refused to take off his viking hat. I looked much more "Baby One More Time…" than I did one of the Fab Five, and I knew it, they knew it — we all knew it. Everybody knew that what they were witnessing was laziness mixed with defeat. Why? Because convinced I was too old for Halloween, I had nestled in to a night of music videos (it was the '90s) and door-answering. Then, convinced to go out with my family members, I disgraced Baby, Posh, Scary, Ginger, Sporty, and more importantly, myself. I'm sorry, neighbours.

4. I have no idea (2001)
I know it's very hard to believe, but I was a very moody teenager who had a lot of emotions. So one Halloween, mad that a girl I didn't like was joining me and my friends on our trick-or-treating escapade, I scrapped my "good" costume (of which I have no recollection) for a men's hoodie with fake bruises on my face and a backwards hat. I DON'T KNOW, YOU GUYS. I have no idea. I have literally no clue what that was about. I think I told everyone I was Kurt Cobain which made NO sense because he didn't look like that. Or I was somebody dead . . . ? For sure, my costume was "some beat up man." Are you grossed out? Good, you should be. Everybody was. Everybody SHOULD'VE been. And the worst part is that I actually had FUN with the girl who came with us, and 15 minutes later felt embarrassed that I'd made such a callous costume choice. (Regardless, I was a "man" because I wore some dude's hoodie and tucked my hair into my hat. So I guess a guy who got in a fight. Let's go with that.)

5. Pamela Anderson (2004)
Hello, I wore a giant pink hat like she wore with Kid Rock that one time, and then a black tank top. That was it. That was my costume. Not even fake boobs or like, a stuffed shirt or a push-up bra. I wore TWO tank tops with built-in bras and then an actual bra, and spent 99% of the night trying to dance sexily with a big pink hat on. These were my choices. "I am a comedy superstar" I remember thinking. "I should enter the costume contest." I did not enter the costume contest. Because if I had, my hat would've sorted me into a new Harry Potter house, reserved only for people who should celebrate no holidays that require effort. And I would've been the only member, I think.

6. Avril Lavigne (2003, 2005)
Not even Avril Lavigne of that time — Avril Lavigne of 2001. And the worst part? I secretly just wanted to dress like Avril Lavigne in 2001; this was just my excuse to give it a whirl — striped arm-sock and all. But it could've been worse (minus forefitting the wig and just ignoring the fact that I had short layers and a borderline shag haircuit) — I could've gone as 2014 Avril. Or worse: Chad.

Tags: errors, halloween, Halloween costumes, mistakes

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