Nate
Everyone has that photo. The one with the chunky highlights, the too-big pants, or the eyeliner applied with absolute emotional conviction. Welcome to the Blunder Years. A glorious time when Gen X and Millennials were out here living their truth in low-rise jeans and questionable haircuts.
These nostalgic pics, shared by brave souls on the internet, are awkward, cringey, and, honestly, iconic. Whether you rocked JNCOs, had a MySpace top 8, or once declared Avril Lavigne “deep,” you’ll feel seen.
Shoutout to everyone who lived through flip phones, Wet Seal, and early webcam angles. These weren’t our best looks, but they were our most authentic.
1. “Me and my sibling crossdressing as a ‘present’ to our mom for Mother’s Day (c. 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.”
2. “Glamor Shots (I Was 12)”
“My parents got a while bunch of free photos of us kids in exchange for advertising with flyers and business cards at their video store next door to the salon that was hosting them. This is probably the most embarrassing photo that exists of me.”
3. “2001 Senior Prom”
“Of course, I was there without a date. Still had a good time.”
4. “2013, the only picture I have of my trip to Chichen Itza”
5. “The early 90s were a vibe”
“Tony Hawk haircut, Doc Martens, Egyptian cartouche, earrings… edgiest guy in my tiny hometown”
6. “My family couldn’t get me to take the costume off”
7. “2007 – wanted to be Hannah Montana and a hippie, but also an Abercrombie model.”
8. “Sophomore year photo, 2001”
9. “Senior pic from 2001”
10. “I want even *that* into Coolio.”
11. “I was a 10-year-old. No one could convince me that cutting my own bangs or wearing a silky robe everywhere were bad ideas. I also liked to daydream about the members of NSYNC fighting over me.”
12. “Graduated 2002… or was it 20002”
“Senior year photoshoot, asked to hold a 2. One too many numbers in there lol”
13. “At 19 (2002) The longer you look the worse it gets.”
14. “15 year old me posing with my stuffed hedgehog on a field trip to DC to because I wanted to show him the White House”
15. “My girlfriend was not playing when it comes to ghost hunting!”
16. “2012 – my first band concert.”
“had a fedora phase. i still own all of 5 of them”
17. “Senior photo ala 2007”
“Epic fog machine and matching lighting color to my bike. The pictures that came out of this shoot are straight out of the early 00’s it’s not a phase era. Enjoy”
18. “Y2K was a strange time for fabrics (Me, 14ish)”
“Apparently I thought this outfit was so special it needed a photo shoot in my family living room!”
19. “2000, 19 Years Old, Stepdad’s Suit”
“Job interview. Didn’t get it.”
20. “I thought I looked so good (‘88)”
“New outfit, mullet and sunglasses. Look out weekend, here I come.”
21. “October 1994.”
“Yes I was a huge fan of The Cure.”
22. “My mother in the 90s”
23. “The only photo that exists of me at my high school graduation, circa 2003”
24. “Sophistication. Confidence. Violin-ence.”
25. “1996, Me with a bowlcut holding 65.000 Danish Kroner”
26. “My friend went to the Bahamas once in 2003”
27. “High school photo, 9th grade, circa 1985.”
“My parents sent me to live with my very conservative grandma on the East Coast who didn’t approve of my West Coast styles (second photo) and so she bought me all new clothes. I think I had about 5 different colors of those sweater vests. You can tell by the look in my eyes that I was dying on the inside.”
28. “Shopping at Claire’s in the mall circa 2004”
29. “I really thought I was doing something with those glasses, 14 years old, circa 2004.”
30. “I was 16 in 2009 and I cut my own hair.”
31. “I thought I was being edgy. (~2006)”
32. “6/87 this scooter was my pride and joy”
“If you thought the overalls were bad, lets look into this ill fitting onesie”
33. “My attempt at long hair circa 1997.”
“Man, I really wish I had been able to commit to the long hair. Just didn’t have the patience to deal with it. Sweet watch though.”
34. “My 1987 high school picture”
35. “Oh, the 90s. Axl Rose is entirely to blame for this nonsense.”
