Back to School: 29+ Hilarious Picture Day Moments Caught On Camera


| LAST UPDATE 02/06/2023

By Arianna Morgan

Yearbook pictures are either a hit or a miss. Some kids blink, some cry, some have bad hair days, and some accidentally show up in pajamas. Let's take a look at some of the most amusing yearbook pics out there.

No More Nap Time?

Picture day rarely goes as planned, and it looks like this little boy woke up on the wrong side of the bed. His face was screaming, "I don't want to be here," but that didn't seem like much of an option...

Yearbook Picture Day FailsYearbook Picture Day Fails
Reddit via u/wrud4d

According to the Reddit user who uploaded the hilarious photo, the picture belonged to her friend's boyfriend, who "was not happy about his kindergarten picture." However, "his parents still have it framed in their house 20 years later," which is honestly hilarious.

Pajama Day or Picture Day?

Look, life's hard at seven years old. Peanut butter or jelly? Spongebob Squarepants or Sonic Boom? Soccer or little league? These are all the hard-hitting questions at seven years old. However, what you wear for picture day isn't usually up to you.

School Picture Day Viral MemeSchool Picture Day Viral Meme
Twitter via @hashtagjules

Picture-day outfits are an integral part of the process. Usually, at seven years old, parents are in charge of picking the perfect outfit for the day, but things can get complicated when mom mixes up pajama day and picture day - like this mom did. And just like that, you're the kid wearing pajamas on picture day...

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So, as it turns out, this was the retake of this little guy's second-grade photo. He looks absolutely petrified of whatever was happening on the other side - but he also was really trying to smile through it! We can only imagine what his first photo looked like then…

Hilarious School Picture Day FailsHilarious School Picture Day Fails
Reddit via u/blondofblargh

Maybe the moral of this story for some is just to leave the photos as they are. Not everyone is meant for the camera at the end of the day. This also does make us wonder what his third-grade pictures looked like. And, more importantly, did he need a retake?

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Smiling 101

There's something about this one that has us cracking up. We've all witnessed the crazy eyes meets crazy smile combination - but there's something about a first grader that's a lot more endearing. LOL. We wonder if his smiling techniques have improved over the years…

Back To School Funny FailsBack To School Funny Fails
Reddit via u/pudgyllamarider

One Reddit user hilariously commented, "This looks like a first attempt at smiling from a person whose only information about smiling is from descriptions they've read in books," and we totally feel that. Step one, show your teeth. Step two, don't let your top and bottom lip touch. Step three, say cheese!

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Christmas in September?

This little guy doesn't look like he's in the Christmas spirit! But also, aren't school pictures normally taken in September? We are curious as to why this yearbook picture ended up with a holiday background, but it doesn't seem like this guy seems to care.

Funny Christmas Card FailsFunny Christmas Card Fails
Instagram via @mrssteff

His mom uploaded the hilarious photo on Instagram, writing, "School pictures today. I hope I don't get a repeat of this gem from 2016." LOL. It almost looks like he was being taught how to smile while this photo was being taken, but he just couldn't be bothered to go all the way.

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Covid Candids

Going back to school during COVID was a complicated time for kids and their parents. No one knew what was going on, but kids did know to listen to their parents! According to this momma, she laid down some strict rules for her son, and well, he followed.

Covid Mask Picture Day FailCovid Mask Picture Day Fail
Instagram via @thebboys5

She told her son, Jax, "Do not take your mask off at school for any reason," and he said, "Got it, never." So when it came down to picture day, Jax decided it was best to follow his mom's instructions and not take the mask off, even for a quick smile. Maybe he's smiling underneath the mask?

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Where Are the Proofs?

Imagine being the mom to this little kid and finding these somewhere at the bottom of his backpack. He clearly was not ready to smile for the camera, but it didn't seem like the photographer was going to wait around any longer. And well, mom decided she was going to do something about it…

Viral Picture Day FailsViral Picture Day Fails
Facebook via Stronajai Miles

Stronajai Miles, this little kid's mom, revealed she contacted Lifetouch School Photography to "figure out what happened and why." Back in the day, the photography company would send proofs for parents to choose from before paying up the big bucks for these pictures - but apparently, that's not how the system works anymore… Sorry, momma!

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This little girl has a hilarious sense of humor. She knew exactly what she was doing during her school photo shoot, and she decided just to give it her all. Some moms wouldn't be thrilled with the final result, but some would find it just as hilarious. So what did Raegan's mom think?

Funny Back To School FailsFunny Back To School Fails
Facebook via Sarah Hurley

According to Sarah Hurley, Raegan's mom, she brought home her school pictures, and she was unsure if she should "ground her or high-five her?" LOL. She followed the caption with #2020. And we totally get that as well. During September 2020, moms just wanted their kids back in school - regardless of how the photos were coming out!

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Camouflage Day

Some picture days go worse than others, and this just might be one of those. Besides the classic blue or red background, some photography studios give parents the option to choose a green screen image to vamp up the picture. But this parent didn't account for one very important factor…

Tacky Greetings Card Funny Tacky Greetings Card Funny
Instagram via @loalyinc

The color of her son's t-shirt! That's right, he was wearing a green t-shirt on picture day, according to his mom's Instagram post, and therefore blended into the green screen image. And well, now he's one giant garden. At least he looks happy about it!

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Caught Between a Smile & a Sneeze

Not every picture day is going to be a good one, and that's just a fact. This hilarious #tbt is proof of that! According to the Instagram user who uploaded her second grade picture day photo, she was just not camera ready! We get it, girl. (Though the result was hilarious.)

Yearbook Picture Day BloopersYearbook Picture Day Bloopers
Instagram via @car_men_lomeli

"Caught between a smile or a sneeze," she hilariously captioned the photo. The photographer managed to capture the split second she was between a smile and a sneeze, and well, didn't let her get a re-take! This is why proofs are always necessary.

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It's Giving Stink Eye

Photographers probably have it pretty rough when it comes to picture day and getting kids to smile. This kid is giving major stink eye. Sorry to whoever was the photographer that day, because we know they could feel it too. But what are they supposed to do?

Yearbook Picture Day FailsYearbook Picture Day Fails
Instagram via @danaandtheboys

So where did this stink eye come from?! The full picture shows him holding a red apple in his hands, so maybe he was just as confused as we are. Why have an apple in a school photo? We understand the whole apple and teacher's pet combination, but he doesn't seem too impressed.

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No Rules Here

According to the Reddit user who uploaded this hilarious photo, "I told my 9-year-old I didn't care what he did in his Spring School photos," and well, "This is what he gave us." To be completely fair, there were no rules here, so why not come up with something goofy?

Funny Picture Day FailsFunny Picture Day Fails
Reddit via u/Lindseyrj7

Not only is he giving a teeth-over-the-mouth, ridiculous smile, but he's serving a crazy hair day as well. Giving that much freedom to a fourth grader is absolutely hilarious, so of course, we're going to rock crazy hair and a matching ridiculous smile!

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No More Smiling!

To be fair, kids have to smile so often for pictures; sometimes, enough is enough. And this little girl has had enough! She was not going to give the photographer another smile for the life of her, so here we are years later with this hilarious gem from picture day.

School Picture Day FailsSchool Picture Day Fails
Reddit via u/homerBM

But perhaps our favorite part? The school even offered to re-shoot the photo after seeing the outcome, but her parents declined. Either her parents have a hilarious sense of humor or just figured these pictures all end up in the trash anyways. Or here…

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Loyal to the Band

Listen, we do understand the power that Evanescence had over us in the 90s and early 2000s. Going Under, Bring Me to Life, and My Immortal will forever be stuck in our heads - and we aren't mad about it. However, this girl took her love for the band to next level.

Funny Picture Day FailsFunny Picture Day Fails
Reddit via u/the-passenger77

"My wife's school picture with her most prized possession at the time," this Reddit user wrote. "An Evanescence CD." Talk about being the ultimate groupie! We can only imagine what the photographer thought when they saw her break out the CD and pose for the camera. LOL.

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Don't Blink

This little guy had almost everything lined up for a successful photo day - he was so close. Looks like he had a collared shirt on, his hair was combed, and he was ready for his close-up! But still, he just missed the mark. So what went wrong exactly?

Reddit School Picture Day FailsReddit School Picture Day Fails
Reddit via u/hornifurhonky

Well, the Reddit user who uploaded the old picture confessed that he was instructed not to blink by the photographer during his elementary school yearbook photos! So, clearly, he followed directions really well, and in response, we got this gem of a photo.

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No Smiles Today!

JCPenny Portrait knows how to play the game. At such a young age, picture day can be rough. Getting a child under five to smile is not an easy task, so when a parent gets back a successful photo, we're considering that a major win! However, the opposite outcome is a lot more common…

Yearbook Picture Funny IdeasYearbook Picture Funny Ideas
Reddit via u/ShkmstrReport

So, instead of getting an adorable school picture, this family got more of a mug-shot-styled photo. LOL. Luckily for them, JCPenny Portrait knows what's up and attached a little note explaining that although they tried their best to get that smile, it wasn't happening. But they're offering free re-dos, so that's something?

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Pictures With Pee-wee

Talk about an awkward phase! We've all been there. Let's cut straight to the chase and address the Pee-wee Herman doll sitting next to this fourth grader. Pee-wee Herman was a huge success back in the '80s - so maybe this was pretty common back in the day?

Funny School Picture DayFunny School Picture Day
Reddit via u/grodylarude

Right. So besides the Pee-wee Herman doll obviously stealing the spotlight, let's discuss the safari-inspired outfit choice here. "Me in the 4th grade, ready to go on some sort of tropical safari with my best friend," the Reddit user hilariously captioned the photo. At least he knows.

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Limited Too Era

If this isn't the jackpot of yearbook photos, we don't know what is. And if this doesn't scream the early 2000s, inspired by Destiny's Child and Britney Spears, again, we don't know what is. From the outfit to the seated chair position and the background, this is yearbook gold.

Limited Too Y2K Style ThrowbackLimited Too Y2K Style Throwback
Reddit via u/GeneralLeeCooll

Fuzzy hats, collared short sleeve tees, patterned loose ties, and velour pants: the dream outfit of every girl in the early 2000s. "I remember going to "Limited Too" and thinking those velour pants were a must," the Reddit user laughed. Ah, Limited Too! The good old days.

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My Little Pony

There's a lot to unpack here, so let's just dive right in. There's the fact that school pictures have an "add pony" option to begin within the first place, that's new to us! But what's even better is that this family obviously had the clothes ready to go!

Hilarious Picture Day Fails Hilarious Picture Day Fails
Reddit via u/midnight-at-noon

Let's not discount the fact that besides the obvious prop of a pony, this girl was handed a guitar to complete the photo. We have to wonder, though, was this all green-screen, or was she actually sitting on a pony for her elementary school yearbook photo?

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Serving Sass

This kid just looks like he cannot be bothered to get his photo taken. We get it; yearbook picture day at school can be tough - and this kid is serving that emotion all over his face. The photographer managed to capture him mid-eye-roll. LOL!

Yearbook Picture Day Eye Roll Yearbook Picture Day Eye Roll
Reddit via u/JaysonChrist

"I just remember my mom was mad because they didn't let me do a retake," he captioned the post. So clearly, his mom was not pleased with the outcome of this picture! But honestly, we can't help but laugh a bit at the final product because we can totally relate!

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Allergy SZN

"Allergies were hitting me hard that day," this Reddit user admitted. Look, allergy season can be challenging! There's nothing like fighting off allergies, but we would hope that the allergies would lay low for just a few minutes during picture day. Right?

Yearbook Picture Day Meme Yearbook Picture Day Meme
Reddit via u/digitlhaze

And then there's the typical '90s boy haircut - it's the bowl cut mixed with the short, unevenly cut bangs. Now, that's a style we're glad went out of style… Not to mention those braces. Braces were cool until lunchtime came rolling around - and then they just were not.

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"What? You don't always have your arm straight out to the side while looking terrified during pictures?" No, actually, we don't usually. But according to this momma, her son does! Sorry, this is the perfect combination of adorable and heartbreaking.

Funny Baby Crying Viral MemeFunny Baby Crying Viral Meme
Instagram via @afisher412

This little guy really just didn't know what to do with himself in this situation. After all, it looks like he was just given a gourd and told to "smile." But something about the large fruit must have really thrown him off if this was the final product...

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Show Some Teeth!

If you ask, you shall receive. This mom was not pleased with her son's first round at photo day (left) and "demanded a retake" (right), according to her son, who uploaded the hilarious side-by-sides. She left explicit instructions for the retake, and well, this is what she got…

Awkward Yearbook Picture Day  Awkward Yearbook Picture Day
Reddit via u/[deleted]

"SMILE! Show some TEETH!" were the instructions! And well, he clearly followed. As it turned out, the left was the one that got framed, and the second landed up in an envelope with a hilarious one-liner at the top. "If this face is special to you today, imagine how you'll feel 10 years from now!"

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No Blinking

Look, not all kids are meant for the camera. Sometimes they simply miss a beat, and it's just going to be okay. This kid had everything going for him, too; he had the nice collared shirt on, his hair was combed, and he was in perfect yearbook stance - but still, here we are.

Hilarious School Picture Day FailsHilarious School Picture Day Fails
Instagram via @caseybrady112091

As for mom? Well, she wasn't expecting this outcome. "When you're super excited to see your kid's school pictures….and then you find this in the packet," she captioned the photo. The smile was on point, but something happened when the photographer said, "don't blink." He blinked.

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Snot Central

This was "Tommy's first school picture," according to his momma. So, of course, the stakes were high. But unfortunately, she didn't get the results she wanted. The photographer decided to just go for the shot and completely ignore the snot coming down his nose. "I love the way they captured the snot glistening on his upper lip," she wrote.

School Picture Day RetakesSchool Picture Day Retakes
Instagram via @pickled.plutonium

"He's 3. Nobody could take a few seconds to wipe his nose??" True! Just grab a tissue, someone, and this could have easily been resolved. Besides the obvious snot dilemma, she also shared that she "paid money for this." Also true. These pictures aren't cheap!

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Blocking the Haterz

This little girl was not interested in having her picture taken! It looks like someone did her hair in the morning, but clearly, she didn't like the final look. Her mom uploaded the final picture and revealed both her daughters decided to keep a piece of hair in front of their faces.

Funny Haircut Fails ThrowbackFunny Haircut Fails Throwback
Instagram via @teammork_est.2003

Assuming the photographer asked the girls to pull their hair back, we do have to wonder how that conversation went. Clearly, these photographers have seen it all, so what's a piece of hair in front of the face to them? It's just another day's work, huh?

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Bad Hair Day

Not all haircuts are good haircuts. Unfortunately, not all barbers are supposed to be barbers as well. We're not sure who approved this look, but it definitely wasn't picture-day ready, according to his momma! She uploaded the picture and wrote, "cute kid. REALLY bad haircut." LOL.

Bad Hair Day FunnyBad Hair Day Funny
Instagram via @juliamboyle

To be entirely fair, she admitted, she forgot that it was picture day, so they "woke up early and went to Great Clips before school," and well, this was the outcome. It almost looks like they ran out of time after shaving off both sides and couldn't even out the middle. But at least he's smiling, right?

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Green Glasses & Green Screens

Good ol' green screen doing its thing! As we've already seen, any green clothing immediately gets picked up by the green screen and morphs into the background. And apparently, the same rules apply to glasses. "Note to self… put Zs black glasses on him for picture days," this mom wrote.

Funny Green Screen FailsFunny Green Screen Fails
Instagram via

"Apparently, the backdrop is bright green, so when they digitally did the backdrop, it got put in his glasses," she wrote. Well, this seems to be a mental note for us all. Avoid wearing green on picture day at all costs because ya never know what you can turn into...

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Teachers Have Bad Picture Days Too

Yearbook photo mishaps are not exclusive to just children. Teachers can have a rough picture day as well. This teacher shared it was her first year as a teacher when this photo was taken, and after the guy took her picture, he told her, "we're all good."

Funny Viral School TeacherFunny Viral School Teacher
Reddit via u/obiwankepuppy

She added, "I didn't think about it again until the yearbook came out," and well, to her complete surprise, this was the outcome! Clearly, the photographer sees the picture after taking it, so why not let her get a quick retake before taking that straight to the printer?

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Tell Us How Ya Really Feel

This must have been this guy's first picture day! As we've seen so far, getting any toddler to smile is hard work, and this kid is no different! In fact, he decided to completely ditch the smile, and go for a completely different facial expression. (Psst, he went with the scowl.)

Funny Baby Greeting Card FailsFunny Baby Greeting Card Fails
Instagram via @allydiebold

It's all in his eyes. We can see he simply doesn't want to be there, and we assume he's letting the photographers know! However, we do get a little glimpse of what could have been a smile with those two little teeth growing from the bottom! Now that's cute.

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