Awkward School Photos That Will Make You Cringe!

School is hard at the best of times. You have to deal with social protocols, heartache and finding your own voice… not to mention the hormones! Throw in the yearly school photo, and added stress and awkwardness are thrown into the works.

Once a year students everywhere get out their best, shiny outfits and brush their hair all in preparation for that dreaded school photo.

Check out these awkward school photos that will make you cringe.

55.) It’s All About the Hair

awkward school photos | giant hair

Compared to the giant hair and big glasses, this kid’s face seems so small.

I hope the hair calmed with age and this was just a phase.

54.) Business at the Front and Party at the Back

awkward school photos | mullet braid

This student seems full of smiles for school photo day. With a hairstyle that allows for epic sideburns and braids at the back, what’s not to be happy about?

I wonder if they stuck to this hairstyle or opted for something a bit more conservative when they got older.

53.) The Ventriloquist Dummy

awkward school photos | boy with dummy

With his sleek back hair and best clothes, this boy is ready for his school photo. Oh, wait, what’s that, a puppet…?

To each their own, I guess.

52.) Say Cheese

awkward school photos | funny family photos

CHEESE! Does this look good? Am I doing it right? Will my parents be proud?

Erm, well, this awkward school photo is certainly memorable: one that they won’t forget.

51.) Braids and Scrunchies

awkward school photos | braid loops

There’s a lot going on up top, and paired with the scrunchies and dress, it’s a bit over the top.

It’s safe to say that this hairstyle is most definitely a questionable choice.

50.) The Troll Collection

awkward school photos | girl with trolls

I feel that this awkward photo is more about the trolls than the actual girl. The trolls steal the show! After all, this troll collection is something to be proud of.

I have a sneaking suspicion that these are only a select few trolls from a much bigger collection.

49.) Basket Face

awkward school photos | basket over head

We all have bad hair days, right? This is the perfect way to hide any offending, out-of-place locks as well as creating a memorable school pic.

Or perhaps they were just a little shy. Either way, this certainly does make a great example of an awkward school photo.

48.) Dazzling Dance Troop Attire

awkward school photos | jazz hands

She’s full of glam and glitter and ready to take on the world.

We’ll not tell her she has a hole in the tights right beside the crotch. That will just be our secret. Shh!

47.) I Feel an Evil Plan Coming Together

awkward school photos | evil little girl

This little girl certainly does look sinister. A plan is been hatched in that innocent brain of hers. Watch out, fellow pupils! Goodness knows what she’s got planned.

Excellent!

46.) Overly Excited

awkward school photos | boy with big glasses

This schoolboy seems really happy to be there and getting his photo taken.

I wonder what he looks like now?

45.) When You Can’t Decide Whether to Have Long or Short Hair

awkward school photos | long and short hair at once

When you can’t decide if you want long hair or short hair, get the mullet!

A smile wouldn’t have gone amiss, though.

44.) Hair-Raising

awkward school photos | 80s hairspray head

I’m not sure if this is the look this schoolgirl was going for or if she slept on it funny and it wouldn’t stay down.

Either way, she nailed the typical ’90s look with oversized glasses and exaggerated bangs.

43.) ’80s Glory

awkward school photos | black mullet on little kid

Everything about this photo screams the ’80s: the hair, the glasses, that T-shirt. It’s just too much!

The person may be filled with many regrets as an adult, but there’s no taking back this outfit. What’s done is done, and all we have to show for it is the awkward school photo.

42.) Green Band-Aid

awkward school photos | boy with green band-aid on lip

Ok, so either there’s some kind of hideous mishap under there, or this kid just likes rocking bright green Band-Aids.

Maybe he thought it would catch on… Nope, kid, the green Band-Aid trend without a doubt did not catch on.

41.) I Don’t Want My Photo Taken Today

awkward school photos | sad face photo

School photos are compulsory, so whether you want to or not, smiling, laughing or crying, it’s happening. Kid, just go with it.

I hope she got a hug after such a traumatic experience.

40.) Shocked

awkward school photos | boy with huge eyes

Make sure your eyes are open. Don’t blink!

This kid possibly tried too hard to keep his eyes open when getting his school photo taken.

39.) Bring Your Rat to School Day

awkward school photos | nerd holding rat

Yep, everyone loves to get their photo taken with a rat, right? Erm, no.

However, he seems comfortable with it, and that’s all that matters.

38.) The Half and Half

awkward school photos | flyaway hair

This student may have been a little indecisive and couldn’t decide which hairstyle to go for. The everyday weekday look, or the full-on crazy hair only sported on the weekend look? Which do you prefer?

The right side is surely defying gravity!

37.) Top Gun Style

awkward school photos | Top Gun school picture

Leather jacket, check. Beautiful, bouncy hair, check. That subtly-looking-off-into-the-distance look, check. I’m cool now, right?

I think this kid has watched Top Gun too many times, and his awkward school photo proves it.

36.) The Beloved Braces

awkward school photos | headgear

So many of us had to have braces at school, and so many of us would rather forget.

This student seems fine with it, though; he’s still smiling away.

35.) Soccer and Silver Waistcoats

awkward school photos | soccer and silver vest

Yes, I do love soccer and silver waistcoats and shorts and I will show you all in this amazing photo.

It may have seemed to be a good idea at the time, but this guy may have lived to regret it.

34.) All Smiles

awkward school photos | huge smile with braces

This overly happy student is making a massive effort to show her enthusiasm for school photo day.

Yes, I am pleased to be here!

33.) Red Eye Makeup

awkward school photos | guy with red eye makeup

He’s a rebel in the making, with his shaggy hair and red under-eye makeup.

This student is obviously too cool to smile.

32.) The Bowl Haircut

awkward school photos | bowl haircut

Ah, the bowl haircut, where a bowl was placed on the head and the hair was cut around the edges of the bowl, resulting in this beautiful hairstyle.

It looks like the bowl is still on the head, just made out of hair!

31.) Yes, I Brought My Teddy Bear; What of It?

awkward school photos | teddy bear with headphones

That’s the look of someone who was told that his teddy bear couldn’t be in the photo but he was going ahead and doing it anyway.

The stare of death!

30.) Mini Old Person

awkward school photos mini old person

This beehive hair makes this little girl look like she is dressing up as a grandma for Halloween.

We would love to see what she looks like now a days.

29.) Harry Potter, Is That You?

awkward school photos harry potter

When look at this picture quickly, we thought this was Harry Potter!

Expecto Patronum those glasses away and this picture wouldn’t have been awkward!

28.) John Wayne 2.0

awkward school photos john wayne

Western movies were popular over 40 years ago, but this wasn’t the best idea for a photo.

It seems like he went all out with his costume and the background.

27.) Indecisive Kid

awkward school photos indecisive

Sometimes it’s difficult to choose what color a person should dye their hair.

We give this kid props for putting two different colors AND shaving it.

26.) The Boy Who Killed Wolf

awkward school photos wolves

The awkward school photo is confusing.

The biggest question we have is: did he kill those wolves?

25.) Devil Child

awkward school photos devil child

Was he trying to embody his bad boy attitude?

Was this a dare?

24.) E.T. Phone Home

awkward school photos et

In the 80’s, the movie E.T. the Extra-Terrestrial was a huge hit.

Apparently, this little girl loved the cute little alien so much that he was in her school photo.

23.) Unimpressed

awkward school photos unimpressed

This adorable girl is not impressed by school and the homework that she needs to do.

School can be the worst and she is that learning fast.

22.) Betty White, Generation 2

awkward school photos betty white

The little girl may have watched a lot of Golden Girls back in the day because this looks like a mini version of Betty White.

Plus, we are loving the blue sequin jacket. It’s too cute!

21.) Nasty Boi

awkward school photos nasty

Why are we calling him nasty?

In our opinion, this shirt probably isn’t the best idea to wear on school picture day.

20.) 10 Going on 60

awkward school photos old woman

Awkward Family Photos

The 80’s were a confusing time for everyone, especially for this little girl.

We aren’t sure if she is 10 years old or a 60 year old grandma.

19.) Marvin the Martian Fangirl

awkward school photos martian

Awkward Family Photos

When you are young, you are going to make silly mistake.

Well, this might be one of them. She really liked Marvin the Martian, but the toy takes it to another level.

18.) My Precious Moment

Awkward Family Photos

Gollum might be saying “my precious” about the girl.

It’s a creepy background.

17.) Plunger Lover

awkward school photos plungers

Awkward Family Photos

Some children love to collect barbies, others love to collect rocks.

This little girl loved plungers so much that there in her school picture.

16.) Over It

awkward school photos senior year

Awkward Family Photos

Senior year of high school is always the hardest. Not because of the hard classes, but because senioritis starts to kick in.

This picture explains how we all felt our senior year: 100% OVER IT.

15.) King Henry

awkward school photos king henry

Awkward Family Photos

He fancy, huh? Wow, this is amazing.

Was it school picture day or was it Halloween?

14.) Not Appropriate Job For a Child

awkward school photos poor career choice

Awkward Family Photos

A kid can dream, but this definitely isn’t a dream job you want as a kid.

His parents must have been embarrassed.

13.) Garfield FTW

Awkward Family Photos

The rainbow overalls and the purple shirt don’t match. But the most random part about this outfit is the Garfield button.

He must really like lasagna, eh?

12.) Reading In-between the Lines

awkward school photos pathetic

Awkward Family Photos

Well, this wasn’t what he wanted for his school picture.

We wonder if the school children made fun of him.

11.) FAIL BIG

awkward school photos failure

Awkward Family Photos

This is the wrong shirt to wear during picture day. We wonder if he will live on to be a failure, or if he will be successful.

He will probably be the next Bill Gates.

10.) Fart Breaker

fartbreaker awkward school photos

Awkward Family Photos

Yes, this is supposed heart breaker.

But the way she is sitting makes it look like fart breaker and it’s hysterical!

9.) No Goals

no goals awkward school photos

Awkward Family Photos

When you are a kid, you are constantly by grown ups that you are lazy.

Well, this proves every parent’s point!

8.) Just a Teenage Girl

just a teenage girl awkward school photos

Awkward Family Photos

The way that this photoshoot is set up is so awkward.

What kind of photographer thought this was a good idea?

7.) All of the Shells

shells awkward school photos

Awkward Family Photos

Remember the time in the 1990’s when the shells were everyone’s favorite fashion accessory?

Well, this guy took it a little too far.

6.) Gamer Dude

nerd awkward school photos

Awkward Family Photos

The 1980’s-esque background is weird.

His face? Priceless.

5.) Ho, Ho, Ho

ho

Awkward Family Photos

It’s always terrible when it’s picture day.

Next time, do not wear any shirts with words.

4.) Nature Boy

nature boy

Awkward Family Photos

This is what happens when you wear green on picture day.

Just FYI.

3.) The Evolution of an Emo Kid

emo

Awkward Family Photos

Every teen in the 2000s remembers the emo days.

This kid took it to the extreme.

2.) Air Supply

air supply

Awkward Family Photos

Imagine loving scuba so much that you take a picture of it.

It looks awkward though.

1.) Is That An Angel?

fallen angel

Awkward Family Photos

Continuing with the emo evolution, this is what happens when teenagers wear black.

It seems a bit dramatic.

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