From Awkward Family Photos: “This is a photo of my mom when she was in 6th grade. Not sure who her barber was but they may have been blind.”

Though he can behave well enough to become an international man of mystery. But the garish shirt is another matter.

I don’t think I’d smile with pride if I played the triangle in the marching band. Then again, he may have played other instruments.

From Awkward Family Photos: “My senior yearbook photo, shot in the summer of 1977. My mother handed me her charge card (with a note allowing me to use it) and dared to let me go alone to pick-out my photo attire. She was horrified when I brought home a green leisure suit, sans tie. She marched me back to Montgomery Ward and returned it, and purchased this proper three-piece corduroy suit, in rust, complete with a clip-on tie and matching suede shoes. Not only was I Napoleon Dynamite before he was even born, when I looked at the yearbook photos the next year, most of the boys wearing leisure suits didn’t graduate. Thanks Mom!”

From Awkward Family Photos: “I love this photo because there was no doubt in my mind that I looked absolutely awesome that day. This was my favorite look and I rocked it with zero shame. Incidentally, it would be years before a boy actually liked me, but I was too cool to care.”

From Awkward Family Photos: “Although it was nearly 30 years ago, I remember this day. Specifically, I remember putting a lot of thought into the details of my outfit. I needed to look sophisticated, and mature, but like I still knew how to have fun (hence the bolo tie and homemade fimo clay earrings). My mother helped me achieve this look by graciously allowing me to get a perm on only the top of my short hair, and by choosing my fantastic eye wear.”

From Awkward Family Photos: “The year– 1977. For my 2nd grade class picture, I was determined to wear this hat my Grandmother made for me; after all, it matched the dress my mother picked out for me! This photo is the re-take; when my mom saw the first picture – with the hat – she made me go for a do-over. Needless to say the hat came with that day too. I still stand by my decision.”

From Awkward Family Photos: “When my daughter asks why she can’t wear things she thinks are ‘cool,’ I show her this photo from my freshman year in high school.”

The site states that it’s a senior portrait. But from the lighting, you get the impression she’s dead.

Seems more like he’s posing for a cheap advertisement or Power Point background. I’m expecting to see a brand new product or some cheesy word art any time now.

From Awkward Family Photos: “That was the last time my mom ever did my hair.” And yes, her hair is quite atrocious.

From Awkward Family Photos: “This is my oldest brother. When he came to the states , his first obsession was rock&roll… followed by big hair.”

From Awkward Family Photos: “When my son asks why he can’t get his hair cut in a style he thinks is ‘cool’, I show him this photo from my freshman year in high school.”

Here he stands tall in front of the racist Confederate flag wearing a tux, mullet, and earring. Seriously, if he wore camo, he’d be full redneck.

And he’s not really smiling with dignity either. Nor does he seem near a lake either.

Then again, a lot of kids don’t like their pictures taken. This guy is no exception. But he seems among the few to show it.

At first I thought this was some kind of ad judging by the graphics. As a school photo, it’s utterly messed up.

Yet, shirtlessness goes against the school dress code. As does sunglasses. But good luck telling him that.

From Awkward Family Photos: “My mother got her hairdresser diploma in 1987. I was a poor innocent victim of her experiments. I guess she put a billiard triangle around my head and put some hairspray.”

Little kids shouldn’t have big hair like that. Her parents should’ve waited until she was around, well, 40.

He can’t even smile for the camera because he knows his classmates will laugh at him. For his shirt is utterly tacky.

Yet, this girl seems like she’s about to kick ass in an action movie. So don’t call her pigtails cute.

And having that log between that boy’s legs leaves a lot to interpretation. Not sure if that’s an appropriate pose for grade-schoolers.

Okay, he’s just a comic book fan. Not sure what he’s supposed to be. But he’ll fit right in at Comic Con.

From Awkward Family Photos: “This my son’s school pic after busting his lip. Poor kid rolled off the bed, hit his night stand, and had to get stitches. Then picture day!”

From Awkward Family Photos: “In the truest sense of the term, this is an awkward family photo. Circa 1984. Failing to capture the spirit of my role in the North Stafford High School marching band, dad thought it made sense to stage a photo of me in my uniform … in the woods … in a chair that just happened to be there … and without my sax. Instead, it looks like I am the young regent of Sherwood Forest, perhaps its constable, given the bobby hat.”

From Awkward Family Photos: “In our senior English class we had to make Shakespearean Globe Theaters out of a non-wood material. My group used duct tape. To complete the look for the senior picture, I wore my duct tape dress, shoes, tiara and bracelet. I don’t know how the bowling pin on a pedestal worked into the theme.”

Indeed, that may be what her shirt says. But it doesn’t reflect well on her.

This is an iconic image of awkwardness. So I couldn’t leave it out if I tried.

From Awkward Family Photos: “Just found this gem today. Apparently my mother thought it was appropriate to take me to a rave in a dalmation outfit. Needless to say, I was not happy.”

I mean he’s wearing glasses and an irrepressibly tacky football shirt. Think that explains it all.

However, his fashion sense leaves much to be desired. But he doesn’t care.

I’m sure we all feel this way during school pictures. Most kids just want to get their photo done and get going.

From Awkward Family Photos: “I was 6 years old. My mother was obsessed with me being Annie because I had curly hair. So, she fluffed it up, bought me a red dress and a stuffed dog and had my picture taken. I can’t sing, I can’t dance and had no interest in theater. Hopefully, the photo was enough for her dream.”

Though often placement is everything. This might lead to some rather R-rated interpretations.

Seems like he’s trying to make himself appear as badass as possible. Too bad he doesn’t have hard abs to make it compelling.

From Awkward Family Photos: “This is what happens when Mom goes out of town and Dad is responsible for making sure I am ready for picture day at school.”

Seems more appropriate for a dog or gang member. But he doesn’t see anything wrong with it. Until 10 years later.

Yet if that passion is balloon animals, expect not to get laid in high school. Since they’re kind of cheesy.

Apparently, it’s a mix between a mullet and a weeping willow. The top is just ridiculous.

Funny how he’s sitting on a fold up chair with a soccer ball. Possibly dwelling on life’s biggest questions or soccer as a metaphor.

And I think she probably has split ends. Certainly a photo her kids will laugh at someday.

Well, she’s wearing chainmail. Mostly because she lost a bet. Or is playing Joan of Arc in the school play.

Indeed, he’s carrying a fire extinguisher. Yet, he’s not sure what fire he should put out.

I mean the kid’s wearing a suit, vest, and bolo tie. And he’s holding a banner with a big smile on his face.

Wonder if this is a school photo of Major Kira. Then again, a good school photo might’ve been the last thing a Bajoran would think about under Cardassian rule.

From Awkward Family Photos: “This is probably one of the worst school pictures ever. I must have been laughing when he took the picture. But why would my mom send me out like that with my hair like that, knowing that it was picture day? Everyone who sees it asks me, “Were you on drugs?”, my response was “No!”, but I should have been. I am a fairly good looking guy, I promise.”

Man, she must be a stubborn girl. Yet, she won’t be moved in the slightest.

From Awkward Family Photos: “For my 2nd grade photo I opted for the ‘Satan’s child lawyer’ look.”

E.T. in the movie may be freaky but he’s kind of charming. But the E.T. in this photo outright terrifies me.

After all, she’s wearing a cat vest. And when she grows up, she’ll become one of those crazy cat ladies.

From Awkward Family Photos: “My son became a cowboy over the summer, with a feather boa hat. I love that his loose tooth he wouldn’t let me pull was just hanging for his school picture.”

Reading from this angle, it spells out “pathetic.” That poor kid.

His shirt states “No Goals.” Though it may say more than that. Yet, the camera will only get the top.

From Awkward Family Photos: “Looks like I dressed myself for class photos… My cousin told me Hooters was a donut shop.” That’s what they all say.

She’s even wearing a sparkly outfit. but the hair speaks for itself.

Yep, seems like he’s taking one-way ticket to Flavortown on that one. Can see the flames on his collar.

Actually it’s a school picture from the Ukraine. They seem to take the concept to a whole new level.

Uh, that’s the Playboy bunny. Even more disturbing, since when did they make T-shirts with the Playboy Bunny for 5-year-olds?

Actually, he might just be a normal percussionist. Yet, the expression on his face shows he doesn’t like posing with tiny cymbals.

I don’t know if it’s the lighting, her outfit, or her hair. But that girl’s expression kind of freaks me out for some reason.

Seems like the demons have taken over him and rendered him into a soulless vessel. Or he just got kissed by Dementors.

“With the saxephones a playing./When the low brass starts to drone.”

From Awkward Family Photos: “When the teacher laughs while handing you the picture packet and says they tried everything they could, you know you’ve got a winner. When asked ‘Lilly, why didn’t you smile?’ Her response was simple: ‘I don’t like school and I don’t like to smile.’ And that will tell you everything you need to know about this 4-year-old.”

Let’s hope this is photoshop. Because you can’t trust a kid holding a burning ball.

This bob 1970s haircut is hideous. Why would any parent subject their little girl to that?

From Awkward Family Photos: “When you are 6 years old and have been preparing all morning to pose with your hand on your hip for school pictures, because that is the cutest pose after all, and then are told to put your hand on your chin, suddenly pictures don’t seem as fun.”

From Awkward Family Photos: “I was having my senior photos taken and decided that I wanted something different than everyone else. Something that was fun and wasn’t so cookie-cutter. My friend, who was killing some time with me, got a Druid’s cloak from the trunk of my car, (Who didn’t have one of those in their car? It was the 90’s after all), and lurked around in the background. I dunno, I kind of like it.”

Apparently, parents at the time thought such hairstyle was cute on their children. But I think it makes this little girl seem like she’s going to haunt your dreams.

You’d almost think she was straight out of Little House on a Prairie. Save for the top of her hair.

Wonder what’s keeping him down. School picture day? Family troubles? We may never know.

And here he stands for the picture all proud of himself, too. And yes, he’s a redhead with glasses.

I don’t like to stereotype but his short shorts aren’t helping one it. Seriously, you can see the pockets.

In true MC Hammer fashion, she wears sunglasses and a baseball cap. But you can’t touch this.

Indeed, she has a collection of troll dolls. And all clad in the same dress as she is.

Sure he’s only about 9. But already he thinks he’s the biggest guy on campus.

I believe he’s not wearing any face paint. Yet, his hair goes in all directions.

Actually, I might beg to differ. Yet, it seems this girl can’t really decide among the crap below.

However, I don’t think a shirt like this is appropriate for a school picture. Seems to consist of sex, lies, and video tape.

Yet, I wouldn’t want to pose with Gollum since he needs his precious. Also, he’s been corrupted by the One Ring for far too long.

Yes, he’s holding a rat, which he keeps as a pet. I know it’s kind of weird.

She’s the hippie teacher from Recess. Okay, her hair’s short but she more or less resembles a secretary.

Before cell phones, people talked to each other on cord phones. You also had to memorize numbers, too.

Here he poses with his beloved bear rug. And yes, the bear has sunglasses to match.

Seems like she’s already traumatized by all the playground drama. And she can’t unsee it.

From Awkward Family Photos: “Yeah, so I heard my best friend was made into a meme called the 60 year-old girl?”

Doesn’t help that he’s wearing a pink shirt and a sweater vest. Perhaps he knows he’s going to be beat up at school over his outfit.

Wonder how she got her harp near the waterfall. Since they’re quite huge.

From Awkward Family Photos: “A gem I found of my sister-in-law. I will call her ‘Razz-A-Ma-Tazz’ for her upside-down shades.”

From Awkward Family Photos: “This is my sister’s school photo in 1971. My Mom insisted that she wear and wig and as you can imagine, she wasn’t very happy about it. It was of course great to see your older sister get some pay back for all the torture she had caused me during that period.”

However, his fashion sense is best to be desired. Thinks he’s cool but comes off as ridiculous.

From Awkward Family Photos: “My friend’s Mom mixed up pajama day with picture day. He was not pleased.”

From Awkward Family Photos: “My daughter collected toilet plungers when she was little. None of them ever met a toilet, face-to-face, she just liked them. She always wanted to see the ‘plunger section’ of any given store we went to. She painted the handles on some of them and would frequently line them up as her opening act for the puppet shows she would put on.”

Sure he’s not holding a knife. But a book of pocket knives just makes you wonder about him.

From Awkward Family Photos: “Our 4 year old daughter, who refers to herself as Penny Cat Aurora Leopard Butterfly With No Wings, was greatly anticipating picture day at preschool. She styled her own outfit for the occasion, and when the photographer told her to ‘Smile pretty like a princess’, this magic happened.”

Guess this guy is an avid Carl Sagan fan. And yes, the Milky Way Galaxy is made of “billions and billions” of stars.

Okay, those are doll hands. But they’re nonetheless incredibly creepy.

Don’t want to know what he’s doing with that raccoon. Though I know it’s taxidermy.

Well, she’s trying to smile. But it’s practically impossible for her at this point.