40+ Hilarious Photos That Epitomize How Clueless We Were During Our Blunder Years

By Farah J

Oh, what we wouldn’t give to return to the good ol’ days. We’d scream at our younger selves that we did not look “cool” in that emo cut, panda eyes, or fishnet stockings! Frankly, we would pay up a fortune to go back in time to talk to our teenage selves and tell them that mom was right all along.

Most of us still have those embarrassing teenage photos that can induce a cringe and instant laugh at the same time. But no matter how awkward some of them are, we are glad that we got to explore and be our “real selves” unapologetically in those creatively damned outfits and haircuts!

Today, we’ve prepared hilarious ‘blunder years’ photos that some people decided to share with the world, and it suffices to say that some of our own embarrassing memories came back. All in all, we now believe that our teenage phases universally wrecked most of us!

Christian goth granny

Teenagers and their weird love of emo, punk, or goth culture in the late ’90s and early 2000s is peak nostalgia. Some of the deadpan newly found goths took their outfits to a whole new level, and well, the result was a pretty iconic look.

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This twelve-year-old in ’95 called her goth look in a long black dress “Christian Granny Goth.” Honestly, she looks like what we imagine a goth granny would look like! A wide choker with a cross pendant, black nails, lips, and black boots – what an icon!

Loan shark

Teenagers aside, a lot of us have embarrassing yet interesting childhood stories and photos that give our family something to laugh about when we are discussing memories at the dinner table. And most of them include our weird styling sense!

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Take this little gentleman in an ’80s style mullet and three-piece suit, for example. You can tell right away that he was the loan shark of the family. A rare old soul in the body of a little kid! He sure looks cute, though.

The old soul

Usually, when we are children, we go about wearing shorts and tees or pants and button-up shirts. They were our daily go-to’s. Dresses and frocks with frills were relatively uncommon for little kids to wear when they were playing out in the backyard.

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However, it seems some children are born with an old soul. This six-year-old was way ahead of her time, and you can tell why. The plain dress and cardigan on the kid made her look like a middle-aged woman working in a tax office! 

Panda phase

Ah! The infamous panda phase! Who else remembers this hilarious time when nearly everyone at school preferred to wear an absurd amount of black eyeliner around their eyes and had styled, gelled, and straightened emo hair? That was an interesting aesthetic!

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This person was cringing hard after their dad accidentally came across this high school ID in a closet! The amount of confidence we had back then while looking like this is hilarious! We just wish we hadn’t lost it along with the emo phase because it certainly would have come in handy!

Little fighter

If we sum up our teenage sense of style in one short sentence, it would either be “I think I look cool” or “it’s not a phase, mom!”. We all presented our true selves by wearing “cool” outfits, which now bite us in our behinds!

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This person shared a picture of his little self wearing a karate suit with a black belt posing ever so intensely. Boy, how awesome he must have felt. Though he thought he looked cool then, now it only makes his wife laugh extra hard!

Too cool for old school

Pirate rides are the best Disneyland rides and are often most looked forward to. Some may only enjoy the ride and the rush they give them, while others top it off by wearing costumes specifically designed for the grand event! 

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Take this awesome girl in a pirate costume, for example. She was not even in her teens here, but she believed that she was too cool for a kiddy pirate ride while simultaneously wearing a pirate outfit! How ironic and hilarious is that! 

Punk Bratz

The early 2000s were a weirdly iconic era. People hung out in cliques of their own kind, like wolves! You could see friend groups of popular jocks, cheerleaders, and nerds, and then there were goths and punks wrapped in metal.

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If you don’t know what we are talking about, here’s a pictorial description for you. This group of high school friends felt so cool in their mohawks and metal chains, posing in front of their mom’s van. We think they look more like punk Bratz dolls.

Perm the mullet

Mullets in the ’80s and ’90s were a huge fashion trend, and if you are a millennial, you surely went through that phase where you cut all your hair in an attempt to replicate this style. We know we did!

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This guy shared his “Patrick Swayze” style picture with the world, and he, along with everyone else, thinks that his permed mullet hairstyle made him look more like a modern-day lesbian biker! What do you think of that strangely specific assessment?

Say cheese!

It certainly would feel like a blessing to be from a country where they don’t ask you to smile for your passport photo. Some countries have this strict rule where the person must be smiling brightly for the picture! Imagine that!

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This person took that command way too seriously when they were asked to open their eyes wide and smile more. We’re pretty certain that in adulthood, they must feel regretful about their teenage passport picture whenever they look at it!

Legally Blonde

There is a reason why we don’t go up to the attic to take out the old photo albums from our teenage years. The pictures are so embarrassing that it makes us want to burn them all. But since we can’t, we simply ignore their existence.

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This person, however, took it upon himself to do that and showed us the reason why the past can be unforgiving! He even shared that he had a blonde mohawk which he got rid of but left the front bangs. Imagine walking around confidently, looking like this!

Willy Wonka at the school dance

Sometimes, all you need is confidence and swag to pull off a “unique” outfit without peeing your pants from nervousness. This useful piece of advice is not only useful for teenagers with questionable style but also for adults. Confidence is key, people!

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Take this fashionista, for example. Even if they cringe at their outfit choice for their annual high school dance now, they certainly seemed to have enough confidence in themselves to charm their date back then with a top hat like “Willy Wonka!”

Hippie kid

Every kid growing into a teenager develops an obsession with an unusual thing, whether it is an outfit style, a hobby, or a hairstyle. But decades later, their grown-up versions question their sanity at that age. We’re sure you know what we mean.

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This little hippie girl reminds us of “Phoebe” from the ’90s sitcom Friends. Don’t get us wrong, we adored “Phoebe,” but she sometimes wore the strangest outfits. Plus, you know, the guitar. Anyway, this 9-year-old gave her grown-up version a great laugh when she found this photo!

Legend behavior

Our brains are wired in such a way that when we grow up, they filter out most of the memories that we would very much like to forget because of how cringe they were. But thankfully, that’s why embarrassing photos exist!

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All is usually well until the memory resurfaces through your old pictures! For example, this ultra legend attempted to remove this particular teenage era of her life from her memory when she painted glasses and a smiley face on her face every day! 

Middle school syndrome

If you observe closely, middle school was no less embarrassing than high school. We made some pretty strange, questionable, and regrettable choices back then, which still haunt us in our dreams decades later! There was no escaping middle school demons.

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Middle school syndrome is real, and this guy’s picture is proof. While most of us choose to forget those three weird years, this guy is still haunted by the demon of his sixth-grade self! He was certainly going through some serious stuff.

Punk edition

The person who shared this photo said they were bombarded with the laughter of a modern Gen Z who did not know their aunt went through a panda-punk phase in high school when they showed them this photo. We don’t blame the kid; it’s hilarious!

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Sometimes, the world does not let you forget your embarrassing moments and errors that easily. Even if you burn all your old pictures, beware of your best friend’s children, who may find you in an old high school yearbook someday!

Classy or grassy?

Today’s Gen Z kids won’t know the level of cringe we millennials feel when we stumble upon our high school memories. Though nostalgic, some pictures just make us want to dig our own graves! If you’ve never felt that way, just look at this pic and put yourself in this girl’s shoes!

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Facebook has this thing where it takes us back in time by showing us our memories from years ago, and that’s how this person came across the most cringe picture of their high school. Now we are wondering how and why someone would think grass in fishnet leggings was classy.

Engagement shoot

When we were kids, we all wanted some kind of pet as a best friend. And most of us got one. Usually, it was a dog or a cat, but some people got a goldfish or a hamster. However, keeping turtles was not a trend back then.

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This guy shared their professional photo shoot with their turtle pet when they were a little kid. We can already feel the embarrassment they felt at the nerdy shoot arrangement, which looks more like an engagement shoot than a picture with a pet!

Hello Kitty

Teenagers or not, we have all gone through that phase where we obsessively buy random stuff we think looks cool and do an imaginary fashion show while wearing it. And the money? Well, the fun is in spending more than you earn!

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Just like this guy! He reminisced about his teenage years when he worked part-time at Hot Topic and got into a habit of spending more than he could. His randomly put-together outfit with Hello Kitty fingerless gloves made quite the statement, though!

Halloween goodness

Halloween is one of the days of the year when you get to witness a range of creativity all around. It is amazing to see the costume ideas people come up with. Additionally, it fosters a sense of competition too!

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While some may be mind-blowingly unique and innovative, others may only make you laugh and feel bad for the owner. For example, this guy tried and failed not to cringe at his ’98 Halloween Milkbone costume picture! Why would someone allow you to go outside like this?


Cowboy outfits have always been a signature fashion trend among some sections of the population. Even if you don’t live near a farm or have any sort of connection with the wild west, the hats and boots never go out of style!

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Usually, it is just a phase for young ones. Take a look at this guy’s younger self, who wore a whole Texan outfit with a hat and button-up shirt for his picture. We bet he was wearing stylish cowboy boots for the photo too!

Punk is not dead

We can’t tell what it was about the late ’90s and the early 2000s, but we think there was some kind of punk and emo virus going around that only affected teenagers. Well, sadly, most of us grew out of it.

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This rocking couple of thirteen-year-olds gave us peak nostalgia, though. A spiky mohawk and emo bangs! We used to think we were a bit unique and rare then, but it seems like everyone went through that punk/emo phase! We wonder if they’re still together.

Artist at heart

Some people are artists in spirit and soul. One look at them and you can tell that they are a creative of some kind. They either have a ridiculously artistic vibe and confidence, or they have a weird and homeless look.

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This girl showed off her best friend’s wild teenage soul. Apparently, the girl had posters of Bob Marley on her walls, which somehow explains the picture. What we can’t seem to explain or understand, though, is the poor guinea pig on her head!

Emo hair

We believe we can all agree on this indisputable fact: the first decade of the 21st century was wilder than most. Children, teenagers, and adults alike were all going through some eerie phase trying to fit in the “modern and trendy” world.

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Take a look at this picture of a person in 2010. We vote that this Christmas photo must be made into a family heirloom! Both mother and daughter were clearly going through their emo phase, which explains the black hair with emo bangs and strange dark eye makeup.

Halloween year-round!

When fake vampire teeth first got popular, emo and goth teens were the first ones to get their hands on them. If you were a high schooler at the time, then you must remember students wearing them even on a normal Wednesday in June!

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It was like Halloween all year round! Take this person’s picture at seventeen, for example. Hellraiser tee, pointed metal choker, dark eyeliner, and vampire teeth! Imagine growing up and being haunted by this demonic memory for the rest of your life!

Kid logic

Children sometimes make comments that leave us rolling on the floor. And what makes them even funnier is the serious facial expressions they sometimes have when they are stating their logic. They never even realize it when they are doing it!

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For example, this person left a lot of us gasping for air with laughter when they shared this picture of their five-year-old self on the internet. Apparently, the kid’s logic behind frowning and pouting in the picture was that they were too embarrassed to smile!

It’s a twin thing

There is something special about twin siblings, especially when they are identical. They have this weird ‘telepathic’ tendency, as well as the same sense of humor and a similar preference for most things. But it gets a little unsettling when they are going through their “eras.”

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These twins definitely regret doing this in middle school. They made custom shirts that were a direct burn to themselves and their twin. Not to mention the DIY emo haircut phase they both were going through then! Well, it’s a twin thing.

James Blunt

One look at this, and any millennial can immediately tell who this couple in black is posing as; the iconic movie poster of legendary James Bond! This young teenage high school couple must have improvised the pose because this is pretty awkward.

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The James Bond movie series used to be a blockbuster and remained on top of the charts for decades. If you can’t relate, you can ask your parents; they probably went through this phase too. Honestly, the couple looks more like James Blunt, not Bond! 

Proud member of the band

When you are in school, you are required to choose some extracurricular activity or join a club. It is necessary as these activities help you grow physically and mentally. Additionally, they can help you polish your innate talents and make friends.

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But one thing that was made fun of in high school was the band group for some reason. They were seen as nerds in band suits carrying drums and flutes. Looks like this girl was one of them, and her grown-up version of sarcasm is certainly on point!

Limited Too edition

Growing up, we all went through roughly every phase in the name of “self-exploration.” Even as kids, we made some seriously messed up choices when it came to clothes, hair, toys, and friends. Luckily, our confidence masked the horror as much as it could.

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The person who shared this is all grown up, but she couldn’t help but laugh at the girl in the photo. She probably felt that she looked like she had walked straight out of the infamous Limited Too catalog for kids!

Senior sweeties

When we say that high schoolers back in the early 2000s were like species from another universe, we are not being dramatic or exaggerating. We promise that we’re saying this with zero judgment since we lived through it too. Today’s teens don’t hold a candle in comparison.

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This person invited us to take a walk down memory lane when he showed us his high school trading cards with an exotic background that he made of himself and his friends. Though we love “Spiderman” and “MJ’s” story, we couldn’t help but cringe at this!

Anime style

Japanese anime haircuts and hairstyles are still trendy among anime nerds. You cannot blame a young teen for wanting to have an anime haircut as a part of his signature look when he was in middle school. That’s just mean!

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This classy kid takes the trophy for having amazingly styled anime hair, though. While everyone else was going through their emo bangs, he was on his way to greatness with his iconic anime spiky bangs! Only real anime nerds will appreciate this.

Goth phase

While punks and emo kids were quite common around high schools in the 2000s, goth kids were a bit rarer. They often lurked in the shadows and were not seen hanging around the common areas with the rest of the school’s population.

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Well, you can tell the reason for their no-show by the look of this person going through their goth phase. As fancy and traditionally gothic as they look, high school folks were not huge fans of the mask. It was way ahead of its time!

The Enid Blyton kid

Enid Blyton is one of the authors who was famous among kids, specifically for her novels. You must have read at least one of The Secret Seven or The Famous Five book series if you were a child fond of reading.

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And if so, you would see that this kid nailed the exact illustration of the kids described in Blyton’s books! With the haircut, the button-up shirt and high-waisted shorts, and a strap watch, he looked like a character straight out of the books in his childhood!

It’s not a phase!

We don’t know why, but the definition of “cool” among teenagers used to be very odd back in the 2000s. Usually, that term was assigned to outfits that were either emo, punk, or rock. Sometimes, hippie outfits joined in on the action too!

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As teenagers, we all remember yelling this statement at least once: “it’s not a phase, mom!” However, as it turned out, it was indeed a phase. This guy put it hilariously accurately. The narrator of all our stories was probably the same.


If you remember the Dr. Seuss movie, Horton hears a who, then you remember “Jojo,” the last son of the mayor. He was an introverted emo, different from everyone else in the town, and he mostly kept to himself throughout the film.

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Doesn’t this kid look exactly like “Jojo?” MySpace was a huge social networking site among teens back then, and frankly, you would find a lot of emo kids with these kinds of profile pictures on their pages. “Jojo” look-alikes all around!


Wait, did you say seven or seventy? Because there is no way this kid’s outfit is like that of a typical seven-year-old! No judgment, but why would a seven-year-old kid choose to wear a skirt and blazer on picture day at school?

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This poster shared their mom’s childhood picture, where she wore an outfit that made her look like a middle-aged secretary on her way to work! We are hoping that it was a “dress up as grandma” day and not a usual weekday!

Cat in a hat

Whenever we see old pictures of ourselves, from age six to our teen years, we can’t help criticizing, judging, or feeling embarrassed of them. Self-love aside, we used to be weird! Luckily, it seems that we are not alone on that.

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This person shared a picture of himself wearing an all-black outfit and sitting in the lounge of a huge house. Nothing grabbed our attention other than the tophat on the kid’s little head, which he was wearing on a random Tuesday. Why? 

Mates or dates?

Senior proms and school dances were the special events that almost every high schooler looked forward to. Everyone would get excited about their outfits and finding people to attend these memorable evenings with. Also, who didn’t look forward to promposals?

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This dude must have been feeling awesome that evening in this tuxedo t-shirt with a flat-billed cap as a cherry on top. However, we bet this bizarre blunder of a senior prom outfit haunted him for the rest of his evening!

Little mullet bride

Was it just us, or did every kid try to dress up as a bride or groom, wearing the veil and everything we could find in our parents’ drawers related to a wedding? Some of us even had a photo shoot after donning the outfits.

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This person was among the large group of people who wore a bridal gown to church while sporting a mullet haircut! Is she dressed up as a bride, some godly church member holding a Bible, or some hippie in her mom’s veil? Who knows?

Creativity at its peak

When we were kids, we all wanted to grow up as fast as we could. We all wanted to do things for ourselves, especially picking our own outfits. Even though we clearly did not know how to put this freedom to good use.

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This kid is the perfect example of creativity turned into a mess and presented in confidence! We don’t even know where to start; the head wrapped in a paper bag, goggles, or the sweater on top of a flowery dress. However, her proud smile definitely stole the show.


Teenage was the weirdest and the most cringe part of our lives; we all agree on that. We used to wear and do things that even the thought of makes us gag with disgust now. How could we not know how cringe we were being?

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This picture of a thirteen-year-old going through heartbreak and taking a picture of herself with that piece of paper is so dreadful on a personal level that it’s hilarious. We bet the picture is more heartbreaking for her now than the heartbreak itself!

How bad is it?

It is bad enough to have a picture of yourself in a bad outfit, but it is worse if you wore that cringe-worthy outfit on the wrong day! We know this may sound a bit strange, but just look at the picture, and maybe it will start to make sense.

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We’ve never seen such a hilarious collection of bad clothes on one person, but there was a reason for it. This guy’s school had a “dress bad day,” but he got the date wrong. So, imagine his surprise when he walked into the school looking like this and found everyone dressed normally!

First impression

When reporting to a new school or even a new job for the first time, we all take special care in making a notable positive first impression. We put effort into selecting our outfit of the day because it matters a lot.

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This legendary lady shared her goth look on her first day of university. She sure did make a statement there, as well as on the sidewalk! Though we can all agree that she put quite an effort into her look, we can’t imagine doing this every day!

Flower and batman

As far as we remember, during our teenage years, there was no limit to dressing up or the pressure of following aesthetics or fashion trends. Well, there was for some people, but generally, it wasn’t as big of a deal as it is now.

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This person’s young self reminds us of those days. He has a flower in his curls and an edgy batman belt wrapped around his waist. As embarrassing as it is, we love how happy he is in his hula vs. bazinga outfit!

No regrets

The outfits that we wore in our teenage years were nothing but regretful decisions we had to make to be where we are now. It was necessary to do so to find our real selves. Otherwise, we would have been stuck in the cycle of following trends.

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Well, at least this is what we tell ourselves when we come face to face with our past. This person tried to do the same by telling himself that he did not regret his decision to dye his mohawk pink and wear a sleeveless jacket with a leopard print!