30 Throwback Pictures Of 90s And 00s Teens During Their ‘Blunder Years’

I was a teenager in the 90s and 00s, which means there is photographic evidence of choices I would very much like to forget.

Spiky hair, oversized clothes, frosted tips, wallet chains, and expressions that scream “I thought this looked cool.” Every time I see an old picture of myself from that era, I physically cringe and whisper, “Why did no one stop me?”

That’s what makes these throwback photos so comforting. They prove it wasn’t just me. We all went through our blunder years with confidence and absolutely no sense of perspective.

These pictures are a reminder that growing up is messy, fashion is temporary, and someday today’s trends will be just as embarrassing. Enjoy this beautiful collection of peak teen cringe.

1. My good friend Josh showing off his sais in HS. He still says he has no regrets about this. Him and his lovely gf are both redditors. Please bring this to the front page for them.

2. In 2004 I won a contest to DJ at my very small hometown’s easy-listening radio station. I proceeded to play an hour of Evanescence deep cuts and ruined everyone’s morning commute.

3. My favorite photo of my wife as a child, circa 2003.

4. My dad built me this velvet-lined coffin since I was obsessed with Halloween and I used to do my homework in it (2010)

5. 13-14 year old me during my “Eminem phase”. That’s a hairbrush hanging from my lamp and all of my pictures from that time are made black and grey with Gimp. Good times.

6. My friend and I were never invited to parties and we didn’t drink. So we took these photos and posted them to Facebook to look like we did.

7. School photo looking like 60-year old librarian with my cardigan, turtleneck and thick glasses Date and age unknown.

8. Me discovering Photoshop in 2008 was… something else.

9. Me and my twin sister at sophomore formal, you can guess which one is me.

10. With permisson, my partners school photo 2002.

11. 1996 I sewed my own dog vest and I loved it so much.

12. I spent most of my highschool career working at Sonic instead of playing sports. I thought it would be funny to wear a Sonic uniform instead of a Letterman’s jacket for my senior picture. So that happened… 2001.

13. Me in 2004, when all I ever watched was Fight Club and The Matrix while blasting The Prodigy “Smack My Bitch Up”. So cool I had to wear two sunglasses.

14. I learned my lesson about taking a razor to my eyebrows. Big oof.

15. Me in 2009, I called myself Brandon Bloodbath.

16. Hawaii wasn’t ready for my ice cold sister and I in 2003.

17. Me in 2016. I was Melanie Martinez’s biggest fan, I wore blue lipstick and crybaby merch to school every single day; especially for picture day.

18. After living with an extremely awkward senior portrait for 15 years, I tracked down the original photographer, set, and props for a remake that highlights how much I’ve grown as a person.

19. Thought it would be cool to make KNEX body armor.

20. 14 year old me Photoshopping out my dad for Britney Spears. This is just so toxic.

21. I really thought I was a MySpace Queen.

22. Me after I discovered Photoshop in the early 2010s.

23. 2004. Trying to take a MySpace photo while no one was at home.

24. You don’t understand…. I ate UP in 2012.

25. I found my high school id from 2003-2008.. I think this fits here.

26. 2004 family road trip: obligatory angsty teens against picturesque backdrop.

27. My all-time favorite picture of my husband. He was 20 in this picture. Posting with his reluctant permission.

28. I was a 40 year old woman at 13.

29. 1996 HS Yearbook Picture.

30. My mother found this photo of my church friend (Ryan Gosling) and I. We had some Awful 90s hairs cuts.

31. Sophomore year of high school, I would show up like this and hang out behind the library with my little edgy kids group.

32. This is me in 2011, I was thirteen and waited 3 hours in the Arizona heat to meet Freddy from iCarly.

33. Around 2009 I got really into photoshopping myself in surreal ways.

34. Me, a straight female, trying to impress my crush by being one of the guys. I’m on the right.

35. My (conservative Christian) college yearbook Photoshopped my punk rock spikes into a white afro.