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25 School Picture Fails: Awkward School Photos, From Bad Hair to Cheesy Smiles

bad school pictures awkward family photos

Awkward school pictures

School picture fails are almost inevitable – even in this era of digital photography, you can’t escape it!

I grew up in the 80s, so I experienced the ups and downs of the decade’s fashion and hair choices and the school pictures captured what were some very awkward years.

The big hair, the terrible glasses, the less-than-spectacular smiles. It’s all there.

Sadly, my mother carried one particularly bad school photo of me in her wallet for years (we’re talking many, many years), featuring my awkward 8th grade self, wearing a puffy sleeved pink shirt, oversized glasses and the most ridiculous looking perm.

It wasn’t one of my better looks.

Now, with my own kids, I brace myself every year when I get the school pictures back – will they be a success or a total fail? Some years are better than others, but none have been as bad as this roundup of 25 awkward school photos!


  • “I always feel like somebody’s watching me…” 1 of 25
    "I always feel like somebody's watching me..."
    Raise your hand if you had the creepy face on face school pic. Yep, I sure did.
    Awkward Family Photos
  • Cheese? 2 of 25
    Cheese?
    School pictures are no time to work on your Elvis sneer.
    Ellen DeGeneres Show
  • Prairie girl 3 of 25
    Prairie girl
    Was it "Little House on the Prairie" costume day at school?
    Ellen DeGeneres Show
  • Hair fail 4 of 25
    Hair fail
    We'll chalk this up to the 80s. There's no other explanation for that hair.
    Ellen DeGeneres Show
  • Bored 5 of 25
    Bored
    Someone is less than thrilled by picture day.
    Ellen DeGeneres Show
  • Big, big, big hair 6 of 25
    Big, big, big hair
    Remember when big hair was in? This girl wins.
    Ellen DeGeneres Show
  • Nice shades 7 of 25
    Nice shades
    Oversized glasses with the transition lenses and an Izod shirt? Oh yeah, I wore this look as well, circa 1985.
    Ellen DeGeneres Show
  • Pom poms, for the win! 8 of 25
    Pom poms, for the win!
    This girl gets an A+ for effort!
    Ellen DeGeneres Show
  • Ride the wave 9 of 25
    Ride the wave
    Check out that hair!
    Ellen DeGeneres Show
  • Curls aplenty 10 of 25
    Curls aplenty
    Perm-y!
    Ellen
  • The awkward years 11 of 25
    The awkward years
    We're not sure what's worse here… the hair or the glasses?
    Ellen
  • Huh? 12 of 25
    Huh?
    This hair defies gravity.
    Ellen
  • Not happy 13 of 25
    Not happy
    Aw, dolly… why so sad?
    Awkward Family Photos
  • Magical 14 of 25
    Magical
    Reflection, stars. Sigh… dreamy.
    Awkward Family Photos
  • Too much hair product? 15 of 25
    Too much hair product?
    "There's Something About Mary" comes to mind.
    Ellen
  • Fashion forward 16 of 25
    Fashion forward
    She was wearing teeny tiny hats before they were cool.
    Ellen
  • One sided 17 of 25
    One sided
    Woah! There's a lot of hair going on on one side.
    Ellen
  • What?? 18 of 25
    What??
    I do not understand.
    Awesomely Bad School Portraits
  • Anger management issues 19 of 25
    Anger management issues
    Oh man, she is mad.
    1000 Awesome Things
  • Lasers are cool 20 of 25
    Lasers are cool
    Lasers + rainbow dress + saddle shoes = awesome. Right?
    Laser Portraits
  • Pick a winner 21 of 25
    Pick a winner
    One for the grandparents!
    Momland
  • Wide eyed 22 of 25
    Wide eyed
    Trying. So. Hard. Not. To. Blink.
    Awkward Family Photos
  • Super big prop 23 of 25
    Super big prop
    That is one mega super sized pencil.
    Awkward Family Photos
  • Man of many poses 24 of 25
    Man of many poses
    There are no words.
    Awkward School Pictures
  • Maybe smile? 25 of 25
    Maybe smile?
    You've got to commit to the smile, dude.
    Awkward School Pictures

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