80 Cringe-Worthy Childhood Photos That Make People Laugh And Squirm

Jason Sargent Saturday, December 20, 2025

- - 80 Cringe-Worthy Childhood Photos That Make People Laugh And Squirm

Rokas LaurinavičiusDecember 19, 2025 at 6:01 PM

The period is called blunder years, and it hits us either in childhood or adolescence. Basically, it's a time when we think we're cooler than others find us to be. And later, no matter how much we would like to forget our cringey past, there's usually a photo or two to remind us of it. Some are sitting in family albums, some are scattered across our friends' hard drives, and while many try to ignore them, a few decide to spread their embarrassing moments even wider by sharing them on the internet, taking ownership of their previous silly hairstyles and questionable clothing choices.

#1 Here I Am Winning The “Little Miss Piggy” Award At A Mud Volleyball Tournament In 1998

I was sprayed down with a fire hose afterward and wound up with hypothermia.

#2 My Friend Has The Best Awkward Childhood Photo Ever

#3 I Wanted Dreadlocks In Highschool. Mom Gave Me Braids

#4 I Was 10 When I Realized People With No Bangs Had Grown Them Out, Not Cut Them Off

#5 My Family Dubbed Me "Fivehead"

My friends said, "Can you do a brainblast for us?" and "Looks like you have a lot on your mind" when they first saw it.

#6 Apparently This Was The Best Photo They Could Get For My First Christmas

#7 I Recently Visited My Sister Who Shared Her Favorite Childhood Photo Of Me - The Time I Married My Giant Stuffed Pikachu, Ricky

#8 My Uncle Being Embarrassed Of Me Trying To Sip Some Soda In Public

This was at a Hardy’s in Michigan right after we finished a 10-mile bike ride.

#9 My Dad Always Thought This Haircut Looked Incredible On Me. My Mom Thought The Shirt Was Incredible. I'm A Female

#10 I Blame My Mom For This One. My Sweater Wasn't Stained, The Photo Is Just Old

#11 Looking Back To My Iconic Fashion Choices

Year of the last warped tour, earlobe blowouts, Myspace, and getting bullied by the older scene kids.

#12 School Photo Looking Like A 60-Year-Old Librarian With My Cardigan, Turtleneck, And Thick Glasses. Date And Age Unknown

Was born in ‘89 if that helps.

#13 In 7th Grade, I Didn't Have A Date To The Dance, So I Cut Out A Picture Of Brendan Fraser And Taped It To A Stick And Brought It With Me. For Real

I thought my peers would celebrate my ingenuity and hilarity! They...uh...did not.

#14 I Show My Boyfriend One Picture From My Childhood And Suddenly Reproducing With Me Is Off The Table

#15 All Decked Out In Eyeliner And Angst, About To Go To The Local Emo Concert (2006)

#16 In Honor Of National Emo Day, I Thought I’d Share My Favorite Myspace Looks

#17 My 9th Grade "Graduation" In 2002. 3 Months Later I Was In Military School In Texas

I was obsessed with Linkin Park, but yes.

#18 Glad My Wife Changed Hairstyles Since Then

#19 Describe Your Childhood With A Picture. This Is Not The Worst

#20 Glamour Photo From 1994. I Was 8 Years Old (Going On 45 In This Pic)

#21 Yes That Is My Real Head, No This Photo Was Not Edited

The hairstyle is not helping me at all.

#22 2004. Trying To Take A Myspace Photo While No One Was At Home

#23 When I Met My Childhood Crush, Jonathan Taylor Thomas, My Face Was Painted Like A Clown

#24 1994, Age 7, First Grade. My Stepdad Says I Wanted My Hair Cut That Way

#25 Apparently I Didn't Know How To Smile In First Grade

#26 I See Your Friend's "Awkward Childhood" Photo, And Raise You Mine. Man, I Was A Looker

#27 I Went To See The Easter Bunny While Sick With The Flu. Can You Tell Which One I Am?

#28 2005, College Freshmen, Full Of Rebellion

#29 My Sister Asked Me To Post This For Her. She Asked The Babysitter To Make Her Look Like Ernie. She Loved Ernie

#30 This Is My Wife's Favorite Photo Of Me

#31 1995-1997 My Dear Grandpa Showed This To My Fiance The Night Before Our Holy Matrimony

#32 It's 2013, 14-Year-Old Me Liked Photoshop, Fedoras, And Space

It was probably the only image of "space fedora" on Google images. I hadn't figured out how to flip images in Photoshop at that point.

#33 My Wife And I Apparently Shared A Common Love For Ladders, Denim, And Bangs. Our Senior Years In The Late 90s

We actually met about five years after that. We grew up about an hour apart and she graduated a year before me, proving that this theme was universal.

#34 I Used To Think It Was "Cute" To Dress Up Like My Doll

#35 I Had Liberal Parents And Tried To Rebel With This Haircut. It Backfired

#36 My Original 3rd Grade School Photo (Left). Mom Demanded A Retake (Right) With The Instructions "Smile! Show Some Teeth!" Note Which One Got Framed

#37 I Raise You All, My Sister's And My Most Embarrassing Childhood Photo. I'm The Unfortunate Soul On The Right

#38 I Present To You This Very Caucasian Girl Who Dressed As A Rapper For Halloween

When I was 12 and decided to go trick-or-treating as "Bob Marley" or whatever this is.

#39 2007 Photoshoot In My Grandparents' Bedroom. Not Sure What The Inspo For This Photoshoot Was Or What Emotion I Was Trying To Convey

#40 This Is My Wife Circa 1989, Bless Her Heart

#41 Everyone, Meet My Alter Ego, Kyle

#42 Didn’t Realize Whole Body Photo

The hair was a result of poor brushing during summer swim team, and I had to cut it off. Remember getting dressed that day thinking it was a top half photo, and I’d take the sweater off after the picture, hence the biker shorts. No idea about the gumball machine.

#43 This Is What "Rizz" Looked Like In The 90's

#44 Bringing This One Back. My 9th Grade Picture In 2013. Thanks I Hate It

#45 My Boyfriend And His Mom In 1992

#46 My 9-Year-Old Official Photo For A Tap Dancing Routine Set To "My Boyfriend's Back". Yes, That Is My Real Forehead. Yes, I Have Bangs Now For A Reason

#47 My Friend Was 12 Going On 45

#48 My Graduation Outfit Was A Polyester Kimono I Spent All My Travel Money On At Disney World

This was before going off to study Japanese at university. To be fair, though, encountering some of the people in that department was what started bringing me back to reality.

#49 My Childhood Picture

#50 Permission Has Finally Been Granted To Share My Wife's Glorious Childhood Perm/Greatest Soccer Pic Of All Time

#51 My Husband At 14 Years Old

#52 My Boyfriend's Senior Picture

I swear this picture watches me sleep...

#53 Today I Completed My Master's Degree. To Celebrate My Future, I've Decided To Start By Embracing My Past. I Present My Single Most Embarrassing Photo

#54 Embarrassingly Enough, This Is Not The Only Photo I Have Of Myself With Balloons Stuck Up Under My Shirt

#55 10th Grade Me. My Fashion Sense Dictated T-Shirts And Flannels With Sleeves Cut Off

#56 “Thriller” Dance Routine My Sister And I Put On For Our Parents, Where Being A Zombie Meant You Had Hairbrushes Stuck In Your Hair

#57 My Entire Life Is A Kesha Phase

#58 Mom Asked Me To Model For A “Moody” Photo Shoot. Peak 7th Grade Me

#59 Favorite Picture Of My Husband

My husband gave me permission to share this gem of a photo of him. He believes he was in 3rd or 4th grade, 1986 or 1987.

#60 Childhood Me Thought This Would Look Awesome. I Can't Believe They Let Me Take It

#61 Me In The 90s, Absolutely Thrilled To Be Wearing This Chipmunk Onesie

My mom made me wear this to meet Chip and Dale in Disneyland Paris, in the sweltering heat. It’s a miracle I survived. Also, I truly miss having a TV so big that it can fit a photo frame, a haunted porcelain doll, and a giant lamp on it. The good old days.

#62 My Dad Sent Me This Picture The Other Day. I Was 17

#63 Me And My Sibling Crossdressing As A "Present" To Our Mom For Mother's Day (2004)

I'm the one on the left. I really couldn't tell you why, but we decided that we could swap wardrobes and present ourselves to our mom as a gift for Mother's Day. Apparently Pringles are for boys. That was intentional. I padded the dress with bars of soap.