“I’ll Never Be This Cool Again”: People Share The Best Pictures From Their Blunder Years (95 Pics)

Going through old pictures usually brings back all sorts of memories. That means both the beautiful times you feel sentimental about and the top-tier cringe-worthy moments. And even though the latter might make you want to disappear into thin air (or close the photo album, at least), looking back at your young self can often be very amusing as well.

Some of the finest examples that can make you laugh and cry simultaneously can be found on the ‘Blunder Years’ subreddit. Dedicated to, in their exact words, “pictures from a regrettable past”, it covers all sorts of disasters, from questionable hairstyle choices (let me remind you, a side fringe bang covering half of your face was a thing back in the day) to the epitomes of “cool” outfits. Today, we invite you to make yourself comfortable and embark on a journey through time, guided by the beautiful messes in these pictures.

#1 Thanks To My Sister, I Completely Embraced Goth Culture In 1998

Image credits: clumsychickadee__

#2 2009, Black Eye Liner & Lime Green Everything. 13 Years Old, Very Questionable Pose With Dads Webcam

Image credits: symbolicthoughts

#3 Somehow It Took Me Until My Thirties To Figure Out I’m A Dude Despite Going Through High School Looking Like This

Image credits: maybejolisa

#4 1999 Tony Hawk Phase (Yes, Those Are Shorts…)

Image credits: zephsoph

#5 A Mustache Did Not Look Very Good On Me In Middle School

Image credits: JJ2478

#6 In My Bedroom, 2006. My Sister Was The One Who Wrote ‘Butt’ All Over The Walls

Image credits: alexanfaye

#7 Family Photo. What A Mood

Image credits: puffsaddy

#8 Senior Picture; Gamecube Not Pictured

Image credits: ryly_shane

#9 Oh College. I'll Never Be This Cool Again

Image credits: TrondroKely

#10 1998. That Was A Knock-Off Fubu Shirt That I Bought From A Gas Station

Image credits: roqthecasbah

#11 (Oc) I Was Not A Fan Of That Easter Bunny!

Image credits: kennethdpedersen

#12 1991 Obsessed With Michael Jordan

Image credits: foshi22le

#13 Did Anyone Else Have These Weird Hairy Tops? I Thought They Were The S**t

Image credits: tootyfruitysummerluv

#14 I Guess Being Able To See Is Overrated

Image credits: EmpireEmpire

#15 It Was Not A Good Eyeliner Day, And I Was Trying To Make “Hippie Bands” My Thing. Rip To My Emo Era

Image credits: Gothblessyou

#16 1997 Hadn't Washed My Hair In 6 Months After Braiding It. Dread Wax Applied Every Day. I Thought That Was How You Started Dreadlocks

Image credits: TH3_G4DFLY

#17 Me Circa 2005 Thinking I Was The Absolutely Baddest Thing Around With My Men’s Camo Cargo Short And Corset Combo

Image credits: Kbeefydubbz

#18 My Senior Yearbook Photo. I Thought That Quote Was So Funny

Image credits: 7fingersphil

#19 Is This A Blunder Or Old School Cool? All I Know Is, I Was Kicking A*s And Taking No S**t

Image credits: maribrite83

#20 Y’all I Thought I Was Cool Taking These Photos For A Anti Bullying Campaign ? I Did Get In A Magazine Thought (It Was A Contest To Submit Photos For Their Stop Think Feel Initiative)

Image credits: Infinitestripes95

#21 Sometime Between 05 And 07, I Remember I Got To Choose The Background And Which Weapon I Posed With

Image credits: shortlegs99

#22 You May Not Like It, But This Is Peak 1998. Korn Poster And Shortys Shirt Says It All!

Image credits: tshaff138

#23 Me When I Was 12 Years Old Buying My First Cd’s

Image credits: thetinycatt

#24 Who'd Take The Red Pill When You Look This Fly In The Matrix? (2000)

Image credits: War_machine77

#25 My “Date” To The Eighth Grade Dance

Image credits: tamenesh

#26 This Pic Won Me “Most Embarrassing” Genx Photo A Few Years Back. Christmas 1989

Image credits: reddit.com

#27 Recovered This Gem From The "Autobiography" I Wrote When I Was 10

Image credits: Dirty-D

#28 Junior Year Of Hs, Apparently I Thought Wearing A Suit Coat Holding A Plastic Sword Was Cool

Image credits: Axel_Rad

#29 This Is So Long Ago And Yes I Worked At Hot Topic

Image credits: dinosaurpixie

#30 In My Mind They Were The Real Deal. Check The Bowl Cut

Image credits: Thricey

#31 This Was Before Big Headphones Became A Thing Again, Maybe 2005. I Wore Them As Earmuffs And Dragged The Cord Along With Me

Image credits: NeedsMoreTuba

#32 The First Time I Put On My Band Uniform— 2011

Image credits: slinque

#33 Me In 2007 -- Idk Why I Tried To Photoshop My Face Off, But My Hair Was Cool ?

Image credits: stoned_seahorse

#34 Me In 2006, Age 16/17.. Big Myspace Vibes

Image credits: stoned_seahorse

#35 Friends Teased Me For This Fb Pfp, But I Knew I Was Iconic

Image credits: seqoyah

#36 My Siblings, Their Former Partners And Me, Ca 2009

Image credits: Enexiel

#37 Me Circa 1995. I Think I Thought I Was Grunge Or Something

Image credits: hoggytime613

#38 Leave Some Ladies For The Rest Of Us

Image credits: youruineverything

#39 Fake Mullet, Delia’s Shoulder Bag, Paramore Tee, Mountain Dew Can. This Was Peak 2007

Image credits: Kdaniesmith

#40 Frosted Tips, Resident Evil Toys, A Jenny Mccarthy Poster Aka Welcome To 1999

Image credits: thomASSpynchon

#41 Thought I'd Share This Gem. 2002. I Was A Ddr Champ

Image credits: merrythoughts

#42 1999 - I Told Dad “I Need Your Clothes, Your Boots, And Your Motorcycle”. Only Got The Clothes

Image credits: TheZone92

#43 Circa 2006-2007. I Thought I Was The Coolest Guy Out There!

Image credits: HappyYoshi2015

#44 Yeah, I Wasn't Proud Of Myself For This Phase Lol

Image credits: CompetitiveAdvance92

#45 Told My Cousin About This Sub. He Sent Me This

Image credits: stadboer

#46 It Was The 80s. I Have No Other Excuse

Image credits: owzleee

#47 My Mom Cut My Hair The Day Before Picture Day (Early 90s). For Picture Day We Curled My Very Short Hair Resulting In This Delightfully Puffy Abomination Where I Insisted On Wearing Earrings So “I Didn’t Look Like A Boy” . The Result Is This Delightful Xmas Ornament That I Get To Look At Every Year

Image credits: teebee431

#48 Last Round Of Blunder Before I Die Of Cringe. Plus Bonus Current Photo

Image credits: ninja_worrier

#49 Haircut From Dad + Kung Fu Shirt From Grandma = ?

Image credits: KongSackStoolfire

#50 Erhmagerd, Gersbermps

Image credits: NessunAbilita

#51 That Weird Al Early 00s Look

Image credits: timconnery

#52 I Remember Being Obsessed With This Popcorn-Lime Green-Halter Top. Who Let Me Go Out Like This??

Image credits: me_arielb

#53 Took A Pic After We Found Our Cat That Got Away (2010)

Image credits: No-Candidate-3555

#54 My Friends And I, Circa 2007. I’m The Guy Throwing Gang Signs With His Green Soda

Image credits: SaltRevolutionary917

#55 Just Found This Banger Taken 08

Image credits: Toshhba

#56 The Classic ‘Hike Up Your Pants Above The Hemline Of Your Shirt To Look Half Naked’ Trick

Image credits: SteezusMCMXCVI

#57 1985, I’m Mr.gender Bender Glam Goth And Club Scene Regular. The Whole Time I Secretly Listened To Thrash Music Lol. Will I Ever Live It Down?!

Image credits: Seanessey

#58 Peaking At The Age Of 13 In 2003 Has Been Tough. What An Outfit. And A Receding Hairline (That Thankfully Grew Back) From Years Of Pulling My Hair Back So Tightly

Image credits: uneasyandcheesy

#59 My Nickname Was "Ronald" In School

Image credits: DannyDublin1975

#60 Mom Was Mad But Admittedly Almost Peed Herself Laughing At The Results

Image credits: NavyNUCa

#61 Looking Like I Just Crawled Out Of The Sewer. With My Baby Brother Circa 2008/9 ?

Image credits: kclct

#62 My Bedroom 11 Years Ago When I Was 14, Be Careful You Don't Hurt Yourself On All The Edge

Image credits: XLNerd

#63 Lion King Sisters 1994 I Was 8 Years Old And Lil Sis 4 . 1st Day School 3rd Grade And Kindergarten

Image credits: Seaepona

#64 The Year Is 2006. A Hs Teacher Tells Your Friend Group To Stop Standing Around His Classroom, So You Sit Instead. So Smart, So Edgy, So Cool

Image credits: lilahcook

#65 Restricted To Loser Hall (And To 2006)

Image credits: infinitychaosx

#66 Mom, It’s Not A Phase

Image credits: inkmaster916

#67 My Brother And I, Late 90s

Image credits: KFCCrocs

#68 My Teenage Years Are The Gift That Keeps On Giving

Image credits: Toshhba

#69 13 Years Old In 2007. Probably Couldn't Get My "Scene Mullet" Right That Day

Image credits: 2thirty8

#70 High School Art Class

Image credits: minthotel

#71 During My Late Teens, I Went Through A "Everything Beach-Y" Phase. My Dad Dug This Photo Up The Other Day And I Cringed

Image credits: _otterinabox

#72 Found These Pics After Losing My Mom In April. Today, I’m Ready To Share These With The World. I’m 44 Years Old Now, So Please Know That The 80’s Were Not A Forgiving Time

Image credits: reddit.com

#73 My Dad In 1982. He Had A Lazy Eye As A Child So He Had To Wear These Huge Rimmed Glasses. I Can’t Explain The Haircut, Though

Image credits: thetownslore

#74 My Mom Wouldn’t Allow Me To Wear This 80s Era Spider-Man Undershirt For Picture Day, But I Snuck It Under My Clothes Anyway

Image credits: Tack-One

#75 I Wish My Mom Told Me I Didn’t Look Like I Was Part Of The Band Kittie, Instead Of Following Me Around The Neighborhood With A Camera For A Photoshoot. I Used My Neighbor’s Black Car To Stand In Front Of At One Point… Yes I Actually Played Guitar

Image credits: forestnymphgypsy

#76 1997 And My Little Tomboy Heart Hated Everything About This Glamour Shot Look

Image credits: luckymama1990

#77 Pls Enjoy These Pics Of My Younger Self And The Obsession I Had W Michael Jackson Lmao

Image credits: miryuh

#78 Me Not Happy At Having To Wear The Traditional Uniform On Ascension Day, A Rare English Tradition Where Everyone Goes Down To The Wells To Worship The Water…

Image credits: bertance

#79 Tumblr Era Circa 2012. I Did Not Listen To Pink Floyd

Image credits: discoheaven97

#80 Just Found These Pictures Of Me At Age 14 In 2009. I Think This Calls For A Rawr Xd

Image credits: qtmae

#81 Christmas 1988. Pretty Sure I Was Listening To Poison: Open Up And Say Ahh On My Walkman

Image credits: lame_comment

#82 I Left The National Anthem In The Rosin Dust At My Friend's Eagle Scout Court Of Honor. (2010)

Image credits: merv1618

#83 1987, We Loved The Cure, 7seconds, The Decedents, The Smiths, Etc. We Taped 120 Minutes Off Mtv Every Sunday Night From Midnight - 2 Am. I'm On The Far Left. Can Believe We Weren't Blind In One Eye After All The Years With The Lopsided Haircuts

Image credits: Acctgrrl

#84 My Hair Was Teased So Much It Had To Be Homeschooled. Wish I Knew Why The Photographer Wanted To Hide My Legs And Feet

Image credits: artisticatrophy

#85 2003. I Smiled Like This In Every Picture Because I Thought It Looked "Natural." I Swere I've Never Harmed Any Animals

Image credits: NSMetroid

#86 I Didn’t Like Rollercoasters

Image credits: THE_FUZBALL

#87 '98 Or '99, Around 16 Years Old. The Coppery Bleached Hair Was Not My Best Decision

Image credits: bailey_1138

#88 My Beany Baby Shame Is Strong (1994)

Image credits: parasocialdude

#89 I Thought I Was So Cool Wearing The Movie Shirt With Mesh Sleeves

Image credits: wat-lady

#90 Dressed In My Easter Best '98

Image credits: theozarksparkman

#91 My Husband And I, Circa 1991

Image credits: Sloth_grl

#92 My 1988 Dark, Moody 'Madonna' Phase

Image credits: EvenLouWhoz

#93 I, Uhh, May Have Put The Life Jacket On A Little Too Tight

Image credits: boddah666

#94 Teachers Were A Bit Different Back In The Day

Image credits: apesusi

#95 Roxanne… You Don’t Have To Put On The Red Tights! Me In 2011 At A Family Picnic

Image credits: donemessedupthistime


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