It’s hard to think of many things out there that can bring as much fun to as many people as Halloween. From kids trick or treating to adults going to wild parties, this holiday is always a blast for everyone who celebrates it. And what kind of a Halloween would it be without a whole bunch of awesome costumes to remember it by? From the spooky to the silly and everything in between, here are 42 stories of some of the most memorable Halloween costumes of all time!
1. The Quest For the Holy Halloween Costume
I once dressed up as King Arthur from Monty Python. A friend dressed as Patsy. We got a coconut and cut it in half. Then we galloped down the street like two cool cats. One woman actually thought that there was a horse in the street.
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2. I Almost Dyed When I Read This One!
I dyed a pair of long-johns skin color and bought a thrift store trench coach. I wore the trench coat over the long johns to make it look like I was in the buff underneath. The costume was cheap to make and several hilarious “streaking” shenanigans ensued over the course of the night.
3. Age Is Just a Number
I dressed up as an elderly man for a Halloween party one year. It was an awesome costume. I had someone put makeup on me and spray my hair gray so that I actually looked like I was at least 60 years old. I heard multiple people ask one another (thinking that I couldn't hear them) who had invited the "old geezer," "grandpa," and my favorite: "that old weirdo."
It was nice, as always, to see how the youth respect their elders, but that particular guy was a jerk anyway. On a brighter note, many of the girls at the party loved it and spent most of the night hanging around listening to stories that I had made up and my old man jokes (you know the kind, those cheesy ones that your grandpa always told you as a kid).
Best costume ever.
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4. Not What He Was Expecting
One year, I went to a Halloween party dressed up as a pregnant nun, which was a really fun costume. At the time, I drank and smoked regularly, so that just added more to the craziness of the costume. One person at the party was so offended by my costume that he told me I was doomed before storming out of the party in a huff. Some people!!
5. Beating Around the Bush
One year, I dressed up as a shrubbery. I happened to have a cheap camo ghillie suit lying around that had full coverage (as opposed to just a full-length cloak on the back). I camo'd up my face and accompanied my two youngest brothers on their trick or treating. I scared the heck out of so many parents and kids by just standing silently on or off to the side of people's walkways and driveways.
Sometimes I crouched down, depending on the bushes on the rest of the property. This scared people because either: A) They were at the door when we walked up, and they couldn't figure out why there was a shrub where there wasn't one before, or...B) I was there as they were walking up, when I would suddenly turn around to follow my brothers to the next house.
One couple got such a kick out of it that they offered me $20 to just stand there and keep scaring the wits out of people walking by; but, alas, I had to watch the youngins, so I, unfortunately, could not accept their generous offer.
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6. Reaching Across the Aisle
I dressed up as former Republican Vice-Presidential candidate Sarah Palin for Halloween just four days before the 2008 election (the one she was running in, for those too young to remember). I had the heels, glasses, hair, and everything. I then went trick or treating in one of the most liberal neighborhoods of Boston. It was awesome.
7. Hear Me Roar
I dressed up as a dinosaur for Halloween the year when I was 5 years old. I absolutely loved that costume. My mom made it for me and I used to wear it just for fun around the house, even long after Halloween had passed each year. Well, that is, I did wear it around the house...right up until the day when I got heatstroke while wearing it. It was made of a really warm fabric and I had been wearing it in the middle of the summer.
As a result, I started to feel sick one day and eventually threw up all over the dining room floor. I had mostly outgrown the costume by that point anyway; but even if I hadn’t, this certainly would have been the last time I’d have been allowed to wear it when it wasn’t Halloween.
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8. All That Work For Nothing!
The Halloween costume that I am most proud of is the one that my sister wore when she was 14 years old. It was an awesome devil outfit, and she sewed the entire thing for herself from scratch. Sadly, my sister was very tall for a 14-year-old—it ended up being the worst Halloween of her life. As a result, she went up to a house that night and the guy who opened the door said "Aren't you a little old to be trick or treating?!"
He then rudely slammed the door shut in her face, leaving her feeling utterly devastated. Unfortunately, thanks to that guy, that year would prove to be the last time that my sister would ever go trick or treating, even though she had just worked so hard on creating her beautiful costume.
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9. I Don’t Even Recognize You Anymore!
One year, my brother and I meant to dress up as the Men in Black for Halloween, but it backfired when all of the older people in our neighborhood thought that we were the Blues Brothers. On the bright side, most of them were so impressed with our costume choice that they gave us each double portions of candy for the entire night.
10. I See-ling What You Did There!
One year for Halloween, I wore a plain white shirt and wrote “Go Ceilings!” on the front of it with a stylish black fabric pen. I was a ceiling fan…
11. Hitting Them Where It Hurts
I grew up in a Wall Street yuppie-type community, so when I was 9 years old I dressed up as an IRS agent for Halloween. I scared many of the folks in my neighborhood out of 35% of their candy.
12. Hail to the Chief
I went out to a party on Halloween dressed up as the President of the United States a few years ago. I even had a group of friends all wear earpieces and suits and follow me around as Secret Service members, complete with one friend who had the nuclear football. Somehow, everyone at the party knew who I was by the end of the night.
13. Changing Your Ways
One year, I dressed up as a goth kid for Halloween. I'm very quiet and shy by nature. As a result, I’m fairly unpopular at my school and I normally just dress in very simple and unexciting ways. As you can imagine, showing up one day in that kind of a costume was totally out of the ordinary for me. My normally light hair was dyed totally black. I wore knee-length black boots with a heel, black jeans, red lipstick, chained gloves, a spiked choker, and multiple fake piercings.
I had never been stared at by everyone before. It felt pretty great!
14. This One’s a Real Riot!
Growing up, I never really had any specific Halloween costumes that were particularly memorable (with the possible exception of a pretty good Elton John outfit that I had one year—an all-pink suit with matching glasses and a crazy hat). Then, about seven years ago, right after the Vancouver Canucks had lost in the NHL Stanley Cup finals and major riots ensued, my friend came up with an utterly brilliant idea. We'd go out for Halloween dressed as a Stanley Cup rioter.
We live in the Vancouver area, so we knew that everyone in the neighborhood would understand the reference. When Halloween finally arrived, he donned a Canucks jersey, tied a bandanna around his face, and brandished a fake Gucci bag over his arm. He got fully into character by getting loaded and trash-talking the Chicago Blackhawks and other teams that our guys had faced earlier that year.
I thought his timing was amazing, and I gained a lot of respect for his fearless guts when I saw him walking up to authorities and joking with them about burning their cars. Luckily, the officers he spoke to all had a good sense of humor about it. Pretty much everyone who saw the costume liked it, and some people even took pictures with him.
Unfortunately, though, there was one guy who took offense to it. We’ll call him the “angry guy.” The angry guy went off on my friend, telling him how disrespectful his costume was to the city and how it was wrong for him to be mocking the riots. He then told him to "take off his mask" (referring to the bandanna around his face). I reacted by arguing "It's just a little lark, a lampoon. He’s not actually a freaking rioter!"
A nearby bouncer was eavesdropping and laughing at the whole exchange. After a while, he came over and told my friend and me that he would have our backs if the angry guy decided to get violent. Finally, the angry guy’s argument completely broke down after he decided to compare the hockey rioters to terrorists. At that point, we all realized that there was no point in even talking to him anymore.
We all wanted to open-palm slap him across the face. In the end, we just walked away and went to a gentleman's club for the remainder of the evening. Good times!
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15. Was Your Mother Mrs. Popper?
When I was 6 years old, my mom made me a super cool penguin costume to wear for Halloween. The mask was a full hood that I could pull over my face, and she even made little penguin feet for me out of felt with heavy-duty elastic to secure them to my sneakers. Unfortunately, I only got to wear the outfit for one year because I couldn't see very well out of the mask and kept tripping on the sidewalk.
My mom was afraid that I would injure myself if I went trick or treating in it again. Nevertheless, the costume was awesome and I totally loved it!
16. Who Lives in a Halloween Costume Under the Sea?
I dressed up as Mermaid Man from SpongeBob SquarePants for Halloween when I was sixteen years old. It was a cheap, quick, and fun costume to make and wear. I got to spend the whole day dragging my feet through school in pink slippers, yelling "Up... Up... and awaaayyy!!" It felt pretty darn awesome! Unfortunately, I could not find anyone who was willing to be my Barnacle Boy.
17. You Might Be a Redneck
Five years ago, I had a lot of fun dressing up as a stereotypical redneck truck driver for Halloween. I had a full potbelly, a painted-on beard, a blacked-out tooth, and a bald cap. When I was trick or treating, I went door to door greeting people by saying "Good evenin', ma'am! My name is Earl the friendly truck driver, and you're a very pretty lady!"
It was especially funny because I was (very obviously) a 14-year-old girl.
18. A Cult Following
This past year, I dressed up as a cult member for Halloween. I had a black hooded robe, pale skin, gouged-out eyes (done with latex, makeup, black mesh, and fake blood), and a spooky symbol drawn on my forehead. When I entered the costume contest at a local bar, one of the judges took one quick look at me and said, "No way, too creepy!" I consider that a win in my book!
19. Who’s Your Daddy?
One year for Halloween, I wore a paper bag with a big question mark on it over my head. The costume was meant to be my father.
20. A Star Is Born
I went out for Halloween dressed up as a constellation when I was 5 years old. My dad had just brought home a whole bunch of tiny little disposable flashlights from his work that they had been planning to throw out, and we superglued them all over some dark black clothes. As soon as the sun went down, we turned them all on and I looked like a group of shining stars.
Well, at least I did until their batteries started to go out one by one…
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21. Politically Correct
When I was in eighth grade, I got a George W. Bush face mask for Halloween and wore it on top of an insane asylum prisoner’s outfit. I grew up in a really political town where the people were not fans of Mr. Bush’s in the slightest. As a result, I was given sooooo much candy that night!
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22. Accent-uating the Positive
This costume was not created by me, but by my sister-in-law. One year for Halloween, she and her friends bought gas masks from the local army surplus store and scrounged together their best approximations of English schoolgirl outfits. Then, they went around knocking on doors and, instead of saying, “Trick or treat,” they asked, "Are you my mummy?"
23. Captain Jack Will Get You a Selfie Tonight
One year, I dressed up as Captain Jack Harkness from Doctor Who and Torchwood. I went to a Halloween show and the MC requested a picture with me.
24. Praise Be to You
One year on Halloween, a friend of mine decided to dress up as Jesus. He then walked into several different churches, one after the other, saying things like "You know, I didn't actually say that!" or "That quote was taken totally out of context!" Some people found it funny, others were just confused.
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25. Holy Water
I dressed up as a priest for Halloween one year. My friends and I decided to hit the bar and you would not believe the number of people who ask you to bless their drinks or confess their sins when you are pretending to be a priest. Someone asked me what I was doing in a bar if I was a priest, in a fully serious tone. I told him that I was an Irish Catholic.
26. Stuck On You
The best Halloween costume I have ever seen was when I encountered an entire house full of people dressed up as Billy Mays at a party one year. For those of you who don’t remember, Billy Mays was the star of many memorable infomercials in the early 2000s, mostly advertising things like super strong adhesives. Speaking of which, the pesky guys in that house kept trying to legitimately sell me Mighty Putty all night long! I guess they took their role pretty seriously!
27. A Play on Words
One year, I took a 12-inch wooden figurine, built a matching upright piano model to scale, and sat the figurine down at the piano. I then carried that around and told people that I was dressed as a man with a 12-inch pianist.
28. A Storm Is Brewing
One year for Halloween, I dressed in all black and carried a spray bottle around, filled with water. When asked what I was, I'd spray the bottle in the air to make a mist and reply, "I'm a dark and stormy night." I got that idea from a Goosebumps book.
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29. Keep It Down Over There!
One year for Halloween, I went out trick or treating dressed as that classic, stereotypical “strict librarian” that you always see in the movies. I basically just wore my regular glasses, put my hair half-up, wore a church-appropriate dress and shawl, carried around an old book in my hands, and shushed every person that I passed on the street.
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30. So Many Celebrities, So Little Time
I dressed up as Snooki for Halloween a few years ago, because I found this spray-on pantyhose stuff that turns my skin orange. I figured it would be a really good novelty costume. I was proud of the way it turned out, but it almost looked more like a combination of Snooki crossed with Kim Kardashian in the end. It was fun nonetheless.
I also went dressed as Elvis Presley one year when I was 8 years old, and I really went all out for that one. My mom even drew the chest hair on me.
31. The Man Behind the Mask
This past Halloween, I dressed up as the grim reaper. I had the mask, the hat, and the robe, and I walked around silently staring creepily at all the people I passed on the street. I was in an unfamiliar neighborhood in a different town with my best friend who was visiting his family, so NOBODY around there knew who I was.
I had countless people compliment me on the costume when I was walking around, and I definitely scared a decent amount of kids. I also kept jumping out at people who rang my friend’s doorbell when he was back home handing out candy. Naturally, almost all of the kids who rang the bell got pretty startled when they first saw me in the costume.
But don’t worry, I made sure that for any kid under the age of 7 who I scared, I would immediately pull up the mask, smile at them, and politely introduce myself before giving them some candy and a high five. This definitely made them feel better, and their parents certainly appreciated the gesture!
I look forward to doing this again next year.
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32. Devil's Advocate
This past year, I went out for Halloween dressed as a very suave devil. I had a slick suit, a red dress shirt, modestly trimmed horns, and a briefcase that glowed red on the inside. I got no less than 17 people to sign a rather ironclad contract for their souls over the course of the evening. I actually worked for quite some time on the wording of the contract and I can't really see any real way out of it, so I think I might literally own a bunch of people's souls now.
I can’t wait to get to the afterlife now!
33. Trick or Treaters Anonymous
One year on Halloween, I had stumbled upon a sticker saying that I was an addict who was part of a “Quit Smoking” campaign. I had to take my little sister trick or treating that night, so I thought it would be funny if I slapped the sticker on and treated it like a costume. When people would ask me what it meant, I’d say, "You a cop?" and look around nervously while holding my bag towards them.
Once they put candy in, I would take off running. I have no idea what people thought of this routine of mine, but I thought it was hilarious. To be fair, I was 15 years old at the time. I would not necessarily recommend copying this, because it's not funny to some.
34. You and I Define "Awesome" Differently...
One year, I dressed up as someone with the Ebola virus on Halloween. Kids were running away from me in tears wherever I went. It was so awesome!
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35. It’s a Beautiful Day in the Neighborhood
I dressed up as Mr. Rogers for Halloween two years ago. I had the cardigan, the tie, the blue sneakers, khaki pants, and even a replica Daniel Striped Tiger puppet that I had ordered from the Children's Museum of Pittsburgh gift shop.
36. Walking Towards the Light
This year, I went trick or treating for Halloween dressed as a concept for a villain in a story that I'm writing. I wore a dark suit with a fake mustache and a top hat with a lightbulb attached to the top of it. Parents were steering their children away from me. It was pretty darn funny! The little bulb on top was actually a plasma bulb that I re-wired to run off a 9-volt battery.
As weird as this whole thing might seem, it turned out to be a great conversation starter!
37. Crushing It
One year, I wanted to dress up as a bunch of grapes for Halloween, so my friend and I blew up a whole set of green and purple balloons and taped them all over our green and purple shirts. It was a lot of fun!
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38. This Looks Like a Job for Superman!
One year for Halloween, I wore a blue Superman T-shirt with a white button-up dress shirt and a tie over it. I then loosened the tie and undid the buttons on the shirt partway. This worked great for me as a medium-built guy with glasses.
39. Thinking Inside the Box
Back in undergrad, I made a robot costume for Halloween one year by simply making a hole in a painted cardboard box and sticking my head through it. It was a ton of fun to wear, and it was always fun to run into other people who had created the same simple costume. The only downside to it was that it was very hard to dance with anyone at parties while wearing it because, you know, you’ve got a huge box sticking out of your stomach…
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40. Spreading the Good Word
Last year for Halloween, I dressed up as an LDS missionary. I combed my hair neatly, wore a short-sleeved white button-down shirt, a tie, and black pants, and road around from door to door on a bike smiling and brandishing a Book of Mormon at my side. It appears that the costume was so convincing that I actually had multiple people lock their doors when they saw me walking up towards them, obviously not realizing that I was merely approaching to trick or treat like everyone else was.
Now, before I get smothered in hate for the potential offensiveness of my costume, let me just say a few things for the sake of clarification. First of all, I created this costume as a dare from one of my Mormon friends, and I meant it as more of a social experiment than as me making fun of their religion in any way. It wasn't intended to mock their faith, just to see how good a job I could do looking like a missionary.
Apparently, I can do a pretty darn good one!
41. An Eye for Fashion
In high school, I went to a private school where we had to wear a uniform every day. On Halloween, they gave us the option of either dressing up in our regular uniform or coming to school in a costume. However, they made it abundantly clear that if we were not coming in a costume, we were still required to come in uniform. Free dress was absolutely NOT an option.
I showed up in free dress (i.e. whatever I wanted), wearing a T-shirt and jeans, and said that I was dressed as a high school student who didn’t go to this stupid school. The principal wasn’t very happy with me, but he was on a power trip all the time anyway so I didn’t really care.
42. The Old Switcharoo
The best story that I ever heard about a Halloween costume was about a group of students who dressed up as elderly folks one year and carried a portable door around with them while trick or treating. At each house they visited, they placed this portable door directly in front of the door that they were knocking on. They posted a sign on the portable door that said, “Please knock!”
So, when the owner of each house would open the door for them, he or she would be met with another door. Once they followed the instructions and knocked on it, the “elderly folks” would politely open it and reverse the roles of the situation completely—commenting on the homeowners’ costumes and giving them candy!
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