50 Completely Mortifying Halloween Family Photos
By | October 27, 2022
Halloween is the time when every day normal people can let their hair down and let their freak flag fly. Want to dress up like Dracula? Go for it? Feel like being a sexy nun? It's now or never. Even though we applaud everyone who goes all in on their homemade costumes, we would be remiss if we didn't point some of the most downright awkward, mortifying, and straight up cringey Halloween costumes from the Groovy era.
The following embarrassing Halloween photos feature kids wearing last minute costumes and adults showing off questionable outfits all in the name of snagging some candy and getting weird with their friends.
The Wages of Sin
We get it. You want to be funny and cool on Halloween but you've got to take your super cute daughters trick or treating. What could be worse? Rather than dress up like a prince or something a little more on brand you throw caution to the wind and dress up as *checks notes* an apocalyptic street preacher? You do you dad.
The Creatures of the Night, See How Bored They Are
We have a few questions about this couple. Did she not know they were going to a Halloween party? Did the young Mr. Dracula here not give her a heads up? Or did she just not want to dress up? Or, and follow us on this, is she in costume and it's so on point that we don't even recognize it as a costume? There are some questions that we'll never have the answers to.
This is why you don't make your own costume
In the 1980s and early '90s the Teenage Mutant Ninja Turtles were everything to young people across America. Those four pizza loving mutated ninjas were the epitome of cool so it's no shock that this kid wanted to be Leonardo while picking up some candy. In the halcyon days of the late '80s the only choices you had to be a Ninja Turtle were a store bought plastic mask that didn't cover your whole head, going in green-face, or building a giant nightmare head. Clearly this kid's parents went with nightmare head. We're not sure if we should be horrified or impressed.
Bram Stoker's Dadcula
Dracula and Mork from Ork, together for the first time and it feels so good. This is a classic cringeworthy family photo that doesn't just make us laugh, it tells a story. There's something really funny about these two getting dressed up as a couple weirdoes to go down to the JC Penny for a family photo. Did they do this prior to Halloween do get the photos in time? Or did they dress up on Halloween to get their photos taken? As funny as this photo is, we respect their Halloween game.
There are people who love their dogs and then there are people who really love their dogs. It's a sweet idea to dress up like your dog but as you can see here the execution leaves something to the imagination. And by "something" we mean a "horrible nightmarescape full of human-sized dogs who can conceivably eat as much wet food as they want."
Anything can be a costume if you're confident enough
The telephone was new enough in the early '60s that we were still obsessed with all of the fun that could be had with this hot new invention. We're completely on board for how weird this looks, but wouldn't it get kind of heavy carrying a phone around on your head all night? What are the odds that this couple was the first to take off their costumes and just sort of hang around the Halloween party? Although, if that's the move then they just had to carry rotary phones around in their hands all night. Bummer.
Just add water
As genius as this homemade Halloween costume is, it's also 100% unhinged to send your kid to school wearing a plastic dome over their head. It's important to remember that this costume is from an era when something like this was not only totally fine, it's worthy of a second place ribbon in a children's costume contest. What do you think won first place, a kid dressed up like a coffee machine?
Tears of a clown
The clown costume really is the easiest thing to dress a kid in for Halloween, but boy howdy is it freaky to see a toddler walking around like this. As unsettling as it is to see a child clown running around your neighborhood asking for candy, would it be even more unsettling if they had a smile painted on their face rather than the frown that they're wearing now? We've all had to be a clown for at least a couple of Halloweens, often because it's just so easy to do. Hopefully one day parents will learn just how strange this look really is.
Ah yes, the famous Halloween costume "Bag Head"
We truly have no idea what's going on in this photo, but if we had to guess this is some kind of grade school Halloween design contest. The strangest thing about this photo (aside from the obvious) is that the kids who are wearing bags over their heads are also wearing other Halloween costumes. Make it make sense.
We come in cringe
The Coneheads were one of the first truly runaway successes of the early days of Saturday Night Live. Featuring Dan Aykroyd and Jane Curtin, the sketch follows a family of coneheaded aliens who attempt to blend in with 1970s suburbia. Dressing up like the Coneheads is honestly the perfect awkward family costume for a group of fun loving nerds. We salute this family for letting their innate weirdness shine through.
We're giving these people a pass because they clearly love their elders, but could they not spend more than two minutes fixing up grandma's face? It's one thing to roll into the retirement center looking absolutely cuckoo-looloo with lipstick smeared across your face, but to then force your dear old mother (or maybe even grandmother) to face the same indignity is just straight up mean. Hopefully we're just projecting and everyone had a great time at whatever freaky clown party they were attending.
Birds of a feather are awkward together
Where do we start with this father-son costume? The elegant bird head dress on the father? The somewhat lackadaisical headpiece that the son has been strapped with? The Ultimate Warrior facepaint that the kid is wearing? Or should we just jump straight to those fingernails? The talons are both incredibly appropriate and incredibly menacing. As cringe as these costumes are it's great to see a dad going all out for his kid.
This costume is still better than what Joel Schumacher brought to the table
In the 1960s Batman was the coolest costumed superhero thanks to the ABC TV show starring Adam West. While this costume is clearly homemade (and there's nothing wrong with that) the one nit we have to pick with it is the incredibly puffy robe that this kid is strapped with. It looks like something that Bruce Wayne would wear while he was hanging out around the Batcave on a night off. Hopefully this young trick or treater didn't overheat while walking around the neighborhood avoiding the Joker on the hunt for candy.
"Groceries" always works as a last minute costume idea
Does anything say last minute Halloween costume like this photo? Even though it's a little low effort we have to admit that dressing your kids in paperbags and covering them with boxes and receipts is pretty genius. These costumes can be put together in seconds and it doesn't matter if they're destroyed when the kids wearing them are inevitably bullied out of all their well earned candy.
The Force is not with this costume
Star Wars has owned pop culture from the moment A New Hope premiered in 1977. Young fans who wanted to dress up like their favorite characters were forced to figure out the best way to pull off their costumes, and cosplaying as Darth Vader definitely has the most problems. Dressing as Luke, Leia, or Han for Halloween is as simple as throwing on a robe or a vest, but it's clear that pulling off the perfect Darth Vader is tough. That being said, how great is it to see this lofi Darth Vader costume in the middle of this super duper late '70s living room? Out of all the photos collected here this is the the one that doubles as a time machine.
Is this a costume or a last known photo?
It's not totally clear if this is a Halloween photo or if it's some kind of frightening Christmas photo with multiple Krampuses (Krampi?), but we love how lofi and exceedingly creepy the entire tableau is. Examining the multitude of switches that these creepy guys are wielding we're guessing that it's a Krampus thing but maybe we should start mixing the Halloween season with the whole angry Alpine demon thing. We're not telling you what to do but it could be fun.
Even executioners need a break
Judging from the light we're assuming that this is a pre trick or treating photo. Well, and the lack of candy in the photo and everyone knows that once you've wrapped up trick or treating you've got to spread that candy around. This is an absolutely hilarious photo, not only because these kids are in their costumes watching TV, but because the older kid is dressed like a medieval executioner. How funny is that kid? That being said, it would be insane to see that kid walking down the street looking for candy with his (hopefully) fake axe.
Someone get Dracula a napkin
Something about this photo just cracks us up. In the 1970s, most of the affordable Halloween costumes that you could buy from a store were either plastic masks or plastic bags with different types of designs. It's not the fault of these children that their outfits don't really make sense, they didn't design these costumes, but what is going on with the little pirate with super hairy arms? Write in if you can help us figure this out because we're stumped.
Scarecrow's off the wagon again
When dressing up for a Halloween party, or just Halloween in general, it's important to ask yourself how much you want to freak everybody out. This Scarecrow costume is both unsettling to look at and kind of mind boggling. Is this a reference to The Wizard of Oz? Or is this person just really into scarecrows? It's hard to know what's going on here and that's what's so awkward about it. The one thing we do know is that this person really likes to party.
We pity the fools who had to trick or treat as Mr. T
In the '70s and '80s Mr. T was THE guy. His gold chains, his mohawk, and his overall gruff yet wholesome demeanor made him a hero to young people everywhere. It makes sense that these two boys would want to trick or treat as their hero even if they have to use spare car parts and household items to match the fabulous look of the star of The A-Team and Rocky III. The awkwardness in this photo isn't from the kids dressing up (that's the whole point of the holiday) but in what we can imagine is the showing of the photo to partners, family members, and random strangers as these boys get older.
Elephant in the room
It's hard to know if we should be impressed or bewildered by this awesome display of cringey elephant Halloween aptitude. There's obviously some craftsmanship going on with this costume. Note the fingernails attached to what we assume is five different gray suit coats all sewn together, that's a great idea, and the ears no this bad boy look amazing, but we can't imagine walking around a party wearing this all night while trying to drink apple cider through that big honking nose.
As a costume this is a C+ but as protective headgear this is an A+
The thing with this family costume is that you either know that they're dressed like Babar, the French elephant who travels to the big city before being crowned as king of the elephant people, or you just think it's a bunch of people wearing freaky looking elephant heads.
Everyday is Halloween
You're either a Halloween person or you're not, and this family photo clearly illustrates that important delineation. As funny as this family photo is, our cold hearts are definitely warmed by the parents allowing their spooky little kid wear such a chilling witch mask. This is definitely a photo that you want hanging above your mantle.
Straight up Jawawful
Some kids want to dress up as Luke Skywalker for Halloween, others want to trick or treat as Darth Vader, not these kids. Rather than make pretend to be the heroes and villains of a galaxy far, far away, not these kids. They threw on some potato sacks and a couple of blackout masks to cosplay as scavengers who don't know a good droid when they see one. Somebody's gotta do it.
Nothing says "last minute costume" like wrapping your kid in plastic
This is rough. How many of us had to deal with this same indignity as a child, dressed in plastic and balloons as some kind ultra wack candy costume, or our dad's clothes with some smudge on our face so we could trick or treat as a hobo? Sure, it's a quick costume that takes the stress out of preparation for the parents, but it adds years of holiday based trauma to our lives.
You wanted the best, you got these two
When Kiss hit rock radio airwaves in the 1970s there was nothing like them. They looked like alien wizards from another dimension, but their music was accessible to everyone. It makes sense that they became the number Halloween costume for children and adults alike in the American suburbs. The thing about Kiss is that even if you can get the makeup right it's a hard look to pull off well. These two definitely have the attitude, but there's something a little off about their attempt to be the hottest band in the world.
That awkward feeling when you have to dress as your chores for Halloween
Oof. There's no way that this kid wanted to trick or treat as a bag of laundry. Obviously it's a drag because you're just walking around in a big sack with a bunch of stuff jammed around your stomach, but the positive is the HUGE Tide box that makes for the perfect container for all of your Halloween spoils.
Nothing beats a low effort costume
When going to a Halloween party it's important to throw yourself into the occasion. There's no need to be cool and throw on a pair of glasses and a mustache (like a certain someone in this photo), that's barely even a costume. That being said, this guy's pearl snap shirt is incredibly cool.
This screams "oh right it's Halloween"
It's hard to be a parent, especially on Halloween. This photo shows the lengths that parents will go to in an attempt to make sure their kids get a chance to be a pirate, wookie, or unicorn. Is this the perfect unicorn costume, no. We don't even know what that would be, but it's a pretty good (if a little silly) attempt at making a girl's Halloween dream come true.
Mr. Peanut comes for us all
This super fun costume shows exactly how things had to be done in the Groovy Era. There was no world wide web where a trick or treater could pick up the perfect giant peanut costume. A trick or treater had to get creative even if it meant that they looked absolutely horrific while going door to door for candy.
On their way to confession
Is there anything more classic than a nun costume on Halloween? Not only is this an easy costume to throw on, but everyone always has fun posing with a person playing a naughty religious character. That being said, aren't these nun costumes a little basic? Shouldn't they have one more thing going on with them? Maybe a pair of Groucho glasses or a foam finger or something. Let's get in the time machine and figure this out.
All hail Octo-Grandma! This spider outfit is classic grandma right down to the four additional arms that are just flopping around. We've never met this person but we get the feeling that she was super fun to be around. If we could we would high five every single one of her six arms.
The biggest problem with this costume is that if you spill food on yourself it's ruined
Okay we'll say what everyone is thinking - the solid white face is incredibly funny to look at. But how else do you get across that you're dressed as the Pillsbury Doughboy? It's hard not to feel for this kid, after all he is stuck wearing white sweatpants and gloves for the duration of the evening. Just one spill of apple cider or a particularly gooey candy apple and the entire outfit is ruined.
The princess and the castle
This is a super cute idea for kid's costume, and a great way to include a brother and sister in a theme, but there's a major flaw in this concept. Whoever's stuck trick or treating in the castle next to the princess get up has to essentially walk around in a giant cumbersome box all night. It's not exactly what we would call a recipe for a great evening but as long as you're raking in the candy that's all that matters.
Want to be a robot? Just crab some cardboard
We've seen it time and time again in these cringey Halloween costumes, a kid stuck in a big box. It may sound like a great idea: a windup robot costume that costs nothing to make aside from a couple cans of silver spray paint, but when it comes time to walk around the neighborhood whoever's wearing this is going to be in trouble. This costume is a recipe for taking a huge tumble, but if it helps get a little more candy then go for it.
E.T. phone the Halloween store and get a new costume
This is an incredibly cute Halloween photo from the early '80s that shows exactly what's so great about trick or treating with your friends and family. We really do love this, but holy moly that E.T. costume is absolutely wild. Never mind that it looks like a bear cub, does anyone think that the costume looks hotter than heck? You're really sweating out the oldies in this outfit. Hopefully the parents brought along a canteen or two.
When you tell your parents that you want to go as an existential crisis for Halloween
We're not really sure what's going on here but hopefully it's a first draft. Is this a Ninja Turtles costume put together with graph paper, or is it a zombie? Whatever the case, kudos to whatever this kid is doing. We love the individual spirit to create something unique (even if we have zero idea about what's going on).
Spider-Man, Spider-Man, can't do whatever a seamstress can
In the Groovy Era it was nearly impossible to find an accurate superhero costume. Kids really had to go out of their way to find something that displayed their interest but also looked unique, and this homemade Spider-Man costume is definitely unique. It's incredibly sweet that this kid's parents went out of their way to make his dreams come true, but the nightmare fuel on display here is undeniable.
Live long and get a napkin
There are pros and cons to every homemade Halloween costume, and this Mr. Spock outfit is no different. Pro: This kid's eyebrows are on point, down to the eyeshadow that he's wearing. Con: The blue sweater is a bullseye for making a huge mess at the Halloween party. Here's hoping that this young Trekkie had a shirt to change into after making such a huge mess.
Oh wow this kid really got hosed in this photo. Not only does he not get to dress up in any kind of costume, but all of the superheroes that he's posing with are off-brand characters that aren't even trying to hide that they're Sam's Club Superman, Spider-Man, and Wonder Woman. The worst part about this awkward Halloween photo is that the kid knows that he's not hanging with the real thing. Sorry little dude.
Did Tinkerbell have that big of a head?
This is the perfect example of the type of costumes that young people were saddled with in the '60s, '70s, and '80s: a big plastic mask featuring a character's face frozen in an iconic look that you attach to your head with an elastic string. This Tinkerbell mask definitely says, "Hey I bought a mask with a character's face," but it doesn't give you any autonomy over your look or the ability to customize. And, clearly, it freaks out whatever dogs you have running around the house.
Who makes their kid go as a toilet for Halloween?
Do we really have to tell people not to send their kids out into the streets of America to beg for candy while dressed as a toilet? It's a funny concept, and it's a great way to hold onto your candy, but if this kid's friends see them walking around looking like the royal throne they'll never let her live it down.
Dressing as a tossed salad for Halloween is fun, it's original, it's a great way to set yourself apart from the crowd. It also means that you're walking around with a bunch of (hopefully) fake lettuce around your waist while explaining your costume to everyone outside of your immediate friend group who's dressed like a witch or a Frankestein or whatever.
We're pretty sure that these kids are dressed up as some kind of trash man pun, or maybe they're just bags of garbage. Not to be too judgmental but there's something kind of mean about sending your kids out into the streets draped in trash. Maybe they were grounded but still wanted to go trick or treating. Or, and this is a big or, they just really wanted to spend their Halloween dressed up like refuse.
Honestly not a bad Underdog
We absolutely love this Underdog costume even if it's leaning a little bit into nightmare fuel territory. Aside from the whole pillow over the head vibe of this look, it's kind of the perfect children's Halloween costume. If this Underdog showed up at your door you'd know who they were, what they wanted, and how much candy to give them (a lot of it!).
This couple asks you to bob for apples at the Halloween party, WYD?
Adults who love Halloween are our people, but holy cow this couple went way too hard for their costumes. Clearly he's a centaur and she's a unicorn, but we still have so many questions. Are they entering a costume contest, or are they just trying to show off to their friends? Did they stop in at their local JC Penny to get this photo taken? It's entirely possible that they just have this set up in their home, if that's the case then we really want to see the rest of the photoset.
And what might this be?
So what exactly is going on here? Is this some kind of Alice in Wonderland thing? Are these two just trying to be as freaky as possible? Whatever the case we definitely feel for the guy who has to talk to everyone out of the mouth of his costume. It has to be nigh impossible to bob for apples or enjoy a frosty adult beverage without spilling all over your face.
Good old fashioned nightmare fuel
No. Just no. Imagine walking down the street during your annual trick or treat and seeing these four horrific masks coming down the other way. That kind of sight is either a fast end to the day or an inspiration to take a right turn and find a new neighborhood. The fact that these are all little kids makes the whole tableau all the more chilling.
And this is why you don't spend too much time on Dagobah
Yoda is looking rough, folks. Honestly, for someone who has to make their own costume this is a pretty good take on everyone's favorite green little Jedi. Our real question is how you breathe in this face covering. Maybe the eyes have breathing holes, but that's not enough space to help you sneak in a little candy (or, um, water) while you're out trick or treating. Oh well, it's just one night a year.
George Orwell would be proud
Conceptually it makes perfect sense to send your family out trick or treating dressed as different farmyard animals, but in practice it looks truly horrifying. The sheep in this trio is getting off easy. Sure they're a little warm, but they don't have a crazy little squashed up nose on their face. We really feel for the girl dressed as a pig here. It's embarrassing enough to say "Hey I'm a pig for Halloween," but to have dirt smeared all over your face is a special kind of cringe.