63 photos from the past that people cringe at now

No one looks back at their childhood photos and thinks they look great in all of them. There are always a few that make us cringe.

The worst ones are usually taken at a time that we thought we looked pretty cool, but now we realize…well, not so much.

Whether we hang onto those photos or our parents have them floating around somewhere, it’s likely you’ll revisit them at some point.

And some folks, like these brave Redditors, have decided to share them with the world. After all, it’s good to be able to laugh at yourself.

1. What a rebel

Okay, I am actually laughing at this. He looks like an angelic little lawyer wannabe, but then there’s those horns.

2. Not much protection

K’Nex were pretty popular for a while. The same idea as Lego, where kids could connect building materials. However, I don’t know that this body armor would be that useful.

3. One of these things is not like the other.

This is a first family photo. Mom admits that it looks like they stole somebody else’s child as a stand-in for the picture.

4. When mom sews.

First of all, that looks like heavy brocade, that you would use for window coverings or sofas. But it has those little beasties on it, and she’s making a little beastie face.

5. This is so lame.

We all probably remember family road trips that we didn’t want to take with her parents. And our attitude was clearly shown in any pictures taken.

6. She learned her lesson.

Clearly, she wasn’t too shy about it at the time. But she says she’s learned never to take a razor to her eyebrows again.

7. Picture day.

I don’t think we ever took things to school with this on picture day to be included in the pic. But this little cutie has her most prized possession, an Evanescence CD.

8. I have no clue

This is his senior year picture. Lots of leather, and then there are the Depends that he is wearing outside his pants? What exactly are we looking at?

9. Senior picture

I kid you not. This is not an employee of the year photo. Someone wore their sonic uniform for their senior picture because they hadn’t played sports and didn’t have a Letterman’s jacket.

10. The kid from UP

He’s not, but that’s who he looks like. This guy says his mom used to dress him up like this when he was little, so he would be easy to spot when she picked him up at the end of the day.

11. I’m sure the shirt didn’t help

Hopefully this is just a snapshot in time, and he did more than sit in his room while in Vegas at 17. He’s too young to gamble and drink, but surely there was something else he could do.

12. Oh, that’s horrifying.

This is what happens when a young girl doesn’t understand the concept of hair growth. Or at least the concept of bangs. She thought the people who had no bangs had cut them off, not grown them out.

13. So much going on here.

Where does one even start? The spiky half-bangs, the chain, or of the laminated mad face on the front of his shirt?

14. What kind of statement is he making?

This is a picture taken from his sophomore year of high school. I would’ve thought that kind of face paint and the mock bloody shirt would be against school policy.

15. So much confusion

So, first, I would swear this was a male. But this is a school picture of a girl from sometime in the late 90s. Where on earth were people dressing like this in the late 90s?

16. Third grade do-over

This shows the original third-grade school picture, and the do-over that his mother demanded, along with the instructions to smile and show some teeth. I think the first one is better.

17. What a face.

Besides the fact that he looks like a senior, it’s difficult to decipher that expression. We’re sure he’s thrilled, but he also could be constipated.

18. Poor Santa

What else could he do in a situation like this? I really want to know if he asked them if they’d been naughty or nice, or if he judged based on their look.

19. She’s cute!

I’m not sure what she’s wearing, however. But I feel like we should be expecting her to start some sort of exercise routine.

20. Wow

How much hair product does something like that take? So that your hair will stand straight up?

21. This poor child.

The hair color is beautiful. That ginger, red is stunning, however, the cut and how it fans out over his aching years is a tragedy.

22. Homecoming picture.

The dress is beautiful and so toned down in comparison to the hair. She says she spent an hour on her hair, and she did that every single day for several years. I wonder when she grew out of this N’Sync.

23. Remember N’Sync?

This is his senior yearbook photo, back when N’Sync with popular. Love the frosted tips.

24. What is up with that hair?

He’s got that Brillo pad business going on at the top that makes no sense. At least I think this is a he. I’m not sure.

25. He says he has no regrets

it’s just a guess, but I think he was into Zelda. And proud to tell the world that in his senior picture.

26. There’s a lot going on here.

She’s sort of like a goth Rainbow Bright. Frankly, we kind of dig it.

27. A blast from his past

I wonder how he feels while looking at these. His mom just unearthed these 18-year-old pictures while doing some cleaning.

28. Every girl’s worst nightmare

this young lady had a chance to meet her childhood crush, Jonathan Taylor Thomas. Except she painted with a clown face when it happened.

29. There are no words

She’s seven, and either involved in some sort of pageant, or this is just an ill-advised glamour shot. But what on earth is she wearing?

30. Complete confidence.

This is a kindergarten picture. How many children of that age look so self-assured, even with a mullet on their head?

31. No cringe here

Well, you and I are probably cringing, but he isn’t. He’s quite proud of that look.

32. At least she’s only eight

And really, she does look adorable. But her parents thought dressing her up as Elton John to play at a Christmas party was a good idea.

33. So proud of himself

Apparently you’re not allowed Mountain Dew in Mormon summer camps. But this young man has just successfully pulled it off.

34. They told him to smile

This is the first-grade school picture. Apparently smiling was something new to him and he wasn’t quite sure how to do it.

35. Well, that’s just… wrong

Where do some people get their ideas? This young girl grew up in a small Midwest town. She took an urban hip-hop dance class, and this is apparently what urban hip-hop looks like.

36. Their pants!

This is a picture of the three brothers from around 1994. Were men still pulling their pants up like that in 1994? There’s so much wrong with this picture.

37. Not ashamed to share

Senior picture, the summer of ‘04. Her mother said she’d regret this in the future, but so far she hasn’t.

38. She’s rocking those sunglasses.

Her family won a free photo shoot at JCPenney in 2001, and she refused to have the picture shot without her sunglasses. I think she made the right choice.

39. He’s a Guitar Hero

The moment you finally beat expert mode on Guitar Hero. Naturally, you want to set your camera timer and take a picture that will immortalize the moment.

40. Good thing she was understanding.

14-year-old girls are so easily embarrassed. I can’t imagine how she felt when her 14-year-old boyfriend from another school burst into her class on her birthday dressed as a clown.

41. What do you care about?

This little guy cared about Charmander. When his class was asked to take something they cared about to school, that’s what he took.

42. Dreaming of Japan

this polyester kimono is her graduation outfit. She purchased it at Disney World before heading off to study for a year in Japan. So does make some sense.

43. It took a bribe

This is his senior class picture. The only way he could make it happen was to bribe the school photographer. I hope that money was worth it.

44. The face!

This is baby’s first Christmas photo. Definitely one to hang onto!

45. I wonder why

This is his prom photo from 2009. He was a sophomore in high school and says that he took school dances a little bit too seriously. And for some reason, he didn’t have a date for prom.

46. Mom isn’t always right.

This is a class photo from about 2002. Her mom said she would regret this look, but she has no regrets.

47. Are those cardboard cutouts?

If they are, they are very lifelike. This is a party for these two young ladies in middle school when twilight was popular.

48. Remember what I said!

This poor little guy, in his second-grade class picture. His mother warned him beforehand not to blink.

49. But she’s clearly happy

She may look back on it now and cringe, but this is probably the highlight of her year. Getting a photo shoot done at the American Girl doll store.

50. Look closely

this is a 12-year-old going for which he thinks is a cool look. But he got in trouble with his mother for using her eyeliner to draw on that goatee.

51. Not a flattering picture

The yearbook committee decided to add this seventh-grade student’s picture to the book. Unfortunately, he’s skipping rope.

52. The original gangsta

Unfortunately we can’t see the ponytail behind him. He went through a phase in his mid to late teens when he just a lot of gangster movies. They made an impression.

53. This isn’t all

Unfortunately we only get to see the picture of his face paint on picture day in 2002. But we don’t get to see is the mop he took to prom.

54. A little bit of everything

A picture from the 90s. He’s got himself a bowl cut, a Game Boy, and some inflatable furniture.

55. This is not wise

I’m sure he thought that wearing two watches looked cool, but it could be problematic. If they weren’t in perfect sync you would always be wondering which one is telling the right time.

56. The hair doesn’t work

Apparently this is his outfit for his high school graduation, and his mother straightened his hair for him. But I don’t think that hair works with that outfit.

57. What was he thinking?

It’s 2004 and this young man is looking for a job. He sends out this resume thinking they’ll hire him for sure. They didn’t.

58. I would run

Seriously. If I saw this person walking toward me on the street, I would get out of the way. She said she wore this for an entire winter—at 27 years old.

59. Ouch!

I hope he wasn’t bullied. This is his outfit for his first day of high school, when he thought dressing like a 70-year-old man was a good idea.

60. Early tech

Kids today don’t know how easy they have it. Try playing a game using a dial-up modem. And maybe taping a phone to your head.

61. The louder the better

another ridiculous senior year picture. He’s got his subwoofers with him. Yes is one of those people that drive around with their car stereos blasting, and this is why.

62. It could be worse.

Kids are often influenced by the look of a celebrity. This sky grew up in Detroit and its founder was a team when Eminem became famous. The look actually suits him.

63. Oh my

Who thought it would be a good idea to let seniors bring props for their senior photos? Especially when their obsession is with a cartoon character?

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Article Sources:

Reddit – r/blunderyears

Reddit – r/cringepics

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