Don’t Mess With These Utterly Ingenious Rule Breakers

August 17, 2023 | Scott Mazza

Don’t Mess With These Utterly Ingenious Rule Breakers

Some rules are made to be broken—and when you’re a kid or a teenager, you learn very quickly that stepping over the line can be one of the most memorable parts of your school experience. Between stapling shirts together, making vending machine runs for friends, and dyeing your hair crazy colors, these Redditors came together to share some of the best ways they rebelled against school rules.

1. Bright Pink

Back in the 1980s there was one kid in my school who was really into the punk scene. He had a bright blue, 6" high, razor thin, stand-up-straight mohawk. The principal gave him detention for being a distraction  and his parting words that day were: "And more blue mohawk!" The next day the kid came in with the same mohawk, only dyed bright pink.

rule breakers

2. Outrunning the Law

When I was in high school, a boy in my class got sent out for being disruptive. Everyone starts doing their work again only to get disrupted by a commotion outside. We all look out of the third-storey window to see the boy running down the school driveway. A few seconds later, one of our teachers was on a pedal bike chasing him. Yes, he outran the bike.

Messed With The Wrong Person FactsShutterstock

3. No Coat

In senior year, my school banned jackets. A friend was cold, wore his jacket to lunch, and the VP told him to take it off. My friend pulls out the student handbook and asked where it said he couldn't wear it. VP flips for a while and ends up showing him the, "...or anything the administration seems disruptive," clause. My friend rolls his eyes but takes off his coat.

Breaking the Rules FactsWallpaper Flare

4. Duct Tape Trench

After Columbine, our school banned black trench coats. For the most part, nobody cared, except the mysteriously gothic "trench coat kid". He had worn a trademark black trench coat every single day because it made him different, and then all of a sudden, the school tells him he can't do that anymore. So, the kid went out of his way to find (or make) different colored trench coats and wore those instead.

My favorite one was covered in duct tape.

Breaking the Rules FactsPeakpx

5. Half Listening

I was at a private school that had rules about the length of boys’ hair. One guy in particular always ignored the rule and the administration would tell him to get a haircut every so often, but he never did. Eventually, when his hair got about down to his shoulders the principal pulled him aside and told him his hair was twice the allowed length and by next week it needed to be shortened by half.

Monday rolls around and when he walked in, I couldn’t believe my eyes. He had half his head shaved, and the other side as long as ever. We were impressed by literal interpretation of the principal's request, but it still ended up with him getting a suspension for a week and he had to shave the other side before he could come back.

Breaking the Rules FactsShutterstock

6. Backpack Ban

Just after the Virginia incident, when I was in high school, the administration banned backpacks and messenger bags. Purses were okay, though. One guy shows up to school with a purse. They suspended him for two days. The next day, most of the guys showed up with purses carrying all of their things. That’s when they lifted the backpack ban.

Worst Christmas Gifts factsShutterstock

7. I’m Wearing It

After September 11, my school made a rule where we had to wear our school IDs. They went overboard quick handing out detention to anyone who didn't wear one. One kid had his ID blown up and put on a shirt. On the back it said, "Yes I'm wearing my ID". He got detention for not wearing it with the shirt.

Breaking the Rules FactsWikimedia Commons

8. Food Fight

Last day of senior year, we started a food fight at lunch. And by food fight, I mean we drew angry faces on an orange and an apple, then faced them toward each other, made a big circle around them, and we all reacted like we were watching a fight. All the security guards ran to break up the fight, only to make their way to the middle of the circle to find two pieces of fruit sitting on the ground.

Breaking the Rules FactsWikimedia Commons

9. Thanks for Nothing

My friend was told in high school by his guidance counselor not to waste his time applying to his dream school because he wouldn't get in. He got super upset and went to the principal, who told him it was the counselor's job to give her best opinion, so he trusts whatever she says. But then, he applied anyway and got in—and really stuck it to the counselor and principal.

He took the acceptance letter, made a copy, and taped them to both the principal and counselor's door with "thanks for nothing!" written on both. He didn't even go to that school, he couldn't afford it, but it was the principle of the matter.

shutterstock_750530569Thanks for nothingShutterstock

10. Who’s Stupid Now?

I had a teacher in elementary school say I was too stupid to do what I wanted. She also told me to my face that I was slow. I just got accepted to a field school for this summer and every day I am tempted to mail her a copy of my acceptance letter with a post it that says, “Who’s stupid now?” But I am a mature young woman and will instead take the high road.

Montgomery Clift factsShutterstock

11. Trading Network

In my school, you were given a suspension if you had Pokémon cards. So essentially, we started a Pokémon card-trading network. If you told a teacher about losing your card, you were not respected. So, one kid decided that he would start putting cards on the teacher’s desk. Never got found.

Burst Out Laughing factsFlickr

12. Sharing is Caring

When I was in grade 7, our last class of the day, students would always bring in snacks. Our lunch shift was way too early in the day, so by the end of the school day we’d all be feeling hungry. And we were all told by our teacher that if we didn’t have enough to share we couldn’t eat in the classroom. One day, almost all of us brought in enough food to share, even with the students that didn’t bring anything in.

We even synchronized the times that we pulled all our food out. Our teacher was clueless. She had no idea what to tell us. There wasn’t any school-wide “no food in classrooms” rule, so she couldn’t run to the principal. Finally, she gave into our malicious compliance and allowed us to share food for the rest of the period.

Teachers Moment of Hope factsShutterstock

13. Dude, Where’s My Class?

We had a French teacher who was really bad and most people barely tolerated. It happened a few times that whoever arrived first would stand outside her door as if waiting for her to show up and unlock it. Then, the rest of the class would just queue up behind them, pretending to believe them. Meanwhile, the teacher would just be sitting inside wondering where her class was.

Parent-Teacher Night factsShutterstock

14. Shoeless Joe

This one guy was wearing shoes against the uniform policy and was asked to put on shoes from lost property. Instead, he went around school barefoot all day.

Retail Moments FactsPixabay

15. New Kind of Bag

Last year, our school fetched in a ban on backpacks and bags in general since they were apparently a "safety hazard". Two days later, some guy in my year comes in carrying his books and pencil case in a microwave. That wasn’t even the craziest party. The guy made national news!

Dumbest Things They’ve Ever Done factsFlickr, HomeSpot HQ

16. Destroying the Evidence

A kid was passing notes, and the teacher caught him and insisted he had to give her the note so she could read it out loud. He ate the note.

Breaking the Rules FactsFlickr,R

17. Morning, Milady

One of my class mates got sent to the office for wearing "gang" colors. All because he had a red marine bandana tied to his back pack. The rest of the year, he wore a pin stripe suit with a vest and carried a fedora.

Breaking the Rules FactsWallpaper Flare

18. Tickled Pink

I went a private school that told me I couldn’t have hair past my neck. I loved having long hair, so I did it anyway. They told me my hair had to change over the weekend, so I dyed it pink, which was also against the rules. Long story short, I’m no longer at that school.

Breaking the Rules FactsPixabay

19. All Information

We had to use school IDs after Columbine. Some genius decided that they should have our picture, name, year, and full address printed on the front and had to be worn on a neck lanyard at all times.

Even when teachers with children at the school complained, the administration didn't want to backtrack. They threatened students who obscured the info with stickers with punishment for "vandalism".

Then suddenly, it all went away. I wouldn't be surprised if the school district lawyer had some concerns.

Breaking the Rules FactsShutterstock

20. Head Accessory

My daughters both went to a Catholic high school. My younger one had a bit of a wild streak. The girls were required to wear a skirt every day to school. My daughter did not care for this rule and wore her skirt around her head one day since the dress code required the students to wear a skirt, just not where. I was told that she was wearing spandex underneath.

That's how my daughter got a new rule added to her high school dress code.

Breaking the Rules FactsWikimedia Commons

21. Ronald McDonald

My elementary school had a ban on extreme hair colors. My brother shows up with firetruck red hair. The principle stops us both as we’re entering the school and she’s going off on my brother. She’s berating him, saying “Who do you know that has red hair like that?” Without skipping a beat, “Ronald McDonald". The principle just grabbed him dragged him into the office.

My fourth-grade brain was in shock that he just one upped a grown up like that. She called my dad and he didn’t care. Months later, my brother went from red to green to purple.

Breaking the Rules FactsShutterstock

22. One Word

This teacher said: "Hey Joe, aren't you supposed to be in class". He just replied: "Yeah". One word. Doesn't look like much in text, but he said it such full acceptance and resolution that the teacher didn't follow up or say anything else. Just... "Okay, got it. You're not going, I'll move on and not waste any more time here" and they kept walking.

Sometimes attitude is everything. Sometimes you can say a lot with a single word.

Dumbest Idea Worked FactsShutterstock

23. Just Like Jesus

I went to a Catholic grade school growing up that had a strict boys’ hair length policy. It couldn’t touch the collar of your shirt and I wanted long hair. So, the principal came in one day to talk to the class, when she was leaving the room she called me out for my long hair in front of my classmates. My response was to point to the cross hanging above the door and say, “Jesus had long hair".

She didn’t know what to say right away and seemed embarrassed. But, then she pulled me outside and yelled at me to get it cut.

Breaking the Rules FactsFlickr,Philippe Put

24. Technically Obeying

In my private school boys were required to wear a collared shirt. It really wasn't enforced, until one day it was. I was wearing a sweater without a collared shirt underneath and I had to go back to the dorm and change. I argued that I didn't look ratty or underdressed at all, but they said rules were rules. The next day I wore a white T-shirt with a collar (cut off from one of my older shirts) stapled to it. It looked terrible, but rules are rules.

Breaking the Rules FactsFlickr,Robert Sheie

25. Pastry Artist

This was prior to smartphones circa 2002. One of my classmates was a regular class clown. He would buy brownies in the cafeteria and roll them up in his hand so they looked like a convincing number two. He would then do all sorts of antics with it. He’d put it on seats throw it at people what have you. Obviously, the school staff caught on and he got in trouble.

This guy didn’t go quietly, though. He was required to sit alone at lunch for the entire school year. There were months left before summer. The one teacher who made sure his punishment was severe made regular rounds of the lunchroom to maintain order. She would pass his lone seat during her rounds. One day, he made another very convincing pastry sourced item and had it ready for her when she passed.

The entire lunchroom was watching out of the corner of their eyes while maintaining an alibi conversation with the people close to them. When she passed, he stood up and snuck behind her and slipped the pastry in her purse that she was carrying on her shoulder and he quickly ran back to his seat. The lunchroom burst into laughter and the teacher had no idea why.

Until later of course. The dude was an artist at rebellion.

Poop FactsShutterstock

26. I’ll Pass

In third grade, my brother did not want to participate in some sort of multiple class activity. He just hung around the edges until a teacher approached him and said, "Now dear, you can't be here without participating". My brother took what she said to heart and waited for a chance to slip away.
He made it about three miles before a family friend noticed him and drove him the rest of the way home.

I remember mom being upset at him, but even more angry at the school for taking four hours to notice he was gone when they took a head count after lunch.


Helicopter Parents factsPexels

27. Title

One day, my friends and I had gotten to school early for an extracurricular event. After the event, we decided we weren't really feeling school that day and decided to do the 3-hour walk home. One of my friends' mother saw us about 2.5 hours into the walk.

Breaking the Rules FactsPxfuel

28. Vending Machine Gopher

We had vending machines outside the buildings, but someone vandalized them, which understandably upset the school board. The machines were put off-limits but could not be powered down due to some kind of contractual obligation of constant availability. In an effort to combat that, faculty were posted at the machines during class changes to prevent purchases.

But, thankfully, no one was posted at the machines during class time. We weren't happy as that was our sole source of caffeine on campus. We decided, “to heck with that” and made purchases during class. Me, being the tiny guy I was, was conscripted to be the buyer. While the teacher was either out of the room or indisposed, I would collect cash and requests, four at a time, and hop out the “emergency escape window” that they had opted to not have an alarm.

I’d then walk to the soda machine and make my purchase. This went on for some time until the drink companies lambasted the school board for not restocking their dwindling supplies. They put two and two together and realized that purchases were still being made (apparently I was not the only gopher) and lifted the ban on my last year.

Twisted Facts # 2Wikimedia Commons

29.  Snowball Battle

It wasn't a big defiant act or anything, but I loved it and it always stuck with me. One day in high school, we had a particularly hard snow. We were certain school would be canceled, but no dice!

No one was allowed to leave the building during lunch. But a bunch of kids ran outside to have a big snowball fight. We all watched as they had an awesome time, and a couple of random kids joined in.

They all got detention, but I know it was worth it. It was so simple and harmless, and I remember it almost 15 years later!

Favorite Childhood Memories FactsMax Pixel

30.  Snow in Texas

So, I went to high school in South Texas, an area in which it almost never snows. For me, this doesn’t mean anything but I have lived in most of the north for my life so I know what it’s like to play in snow. However, somehow it ended up snowing overnight. And by snowing, I mean like what snow looked like in the north-deep and not just thin and watery. These were immensely heavy flakes.

We were all sure that they would cancel school because Texas does not have salt machines or snow plows and the roads were super slick. A lot of parents didn’t want their kids to go to school because they didn’t feel comfortable with a bunch of new high school drivers on ice. Yet, alas they of course did not cancel school. A little rain knocks out our whole district but a foot of snow and nothing.

My mother made us take the bus because although she felt comfortable driving in snow being from Illinois, Texas drivers are more aggressive, and the roads weren’t properly cleared. I took the bus and it was like being on a safari tour. Kids were taking pictures of the icicles on trees, all wide-eyed. It was funny.

Once we got to school, though, the campus looked like a horror zone. No one would go inside and had instead resorted to snow ball fights on the entire campus and parking lots. Once the bell rang, of course no one went inside. I watched from the window as the vice principal went to the front of the school and commanded the kids inside.

Of course, he was getting nailed in his bald head by snow balls. He finally managed to round up the rogue kids and we all went about first period. I had a relaxed teacher who knew no one would pay attention. Since half the class was missing anyway, she let us “act out the civil war” with snow balls and took us outside.

While we were playing outside, we all paused as we heard the fire alarm go off. The school came pouring out for the next two periods. The dude that pulled the fire alarm is a legend and lives on at our school till this day. He did in fact get taken into custody, along with another kid who thought it would be smart to throw ice at a cop.

That was the one time I saw the high school completely not have a handle on anyone.

Stupid Rules Backfired factsFlickr

31. Pick Me Up

It's not really a rebellion against the rules, but a good friend of mine had a special talent to make teachers like him, despite having no respect for the actual school system. He used to study on his own to ace the tests, rarely showed up to classes he didn't like, and still got perfect report cards with high praises from all the teachers. The height of it was when he convinced his homeroom teacher to come pick him up from the beach before an important test.

He eventually went on to have a great career, but if he ever gets into politics, I wouldn't be surprised if he somehow managed to convince everyone that world domination under his rule was their idea.

Breaking the Rules FactsNeedpix

32. Kyle Energy

So, we had this dude Kyle. He looked like a typical low-income kid with long hair, ripped clothes, beat-up shoes, beanies and goofy socks. Now Kyle was a peculiar kid who spent half his time in detention, rarely ever showed up to tests, and when he did, would just straight sleep through them. He was pretty rambunctious, kind of funny, but ultimately was one of the trouble children.

He was a "low flyer" as the assistant principal called him. It meant he got in trouble but not really for anything serious. One of my all-time favorite stories of Kyle was in our World History class. The teacher absolutely hated him. They always got into it, and honestly, the man would talk very patronizingly to Kyle and the dude snapped back.

Our teacher once said, “Get out. Now". Kyle proceeded to go to the other side of the room from the door. When the teacher asked him what he was doing, he yelled, "Getting my back pack and getting out!" There were these cubbies for our bags by the windows, so Kyle grabs his stuff, packs it up, then straight hops out the window.

What follows is the teacher yelling, "What are you doing?!" and Kyle screaming, “I’m getting out!” followed by him dolphin diving out the window. It was surreal. Kyle was suspended, came back a few weeks later, did some more stuff, suspended again, came back, was finally expelled. The dude is seemingly doing okay now.

Worst Teachers factsShutterstock

33. One Piece at a Time

I was in a Christian high school at the time. The day before winter break rolls around and I had packed a few Toblerone chocolate bars and some notes for the teachers I most appreciated. I had the intention of leaving them as a Christmas gift. Before school, the principal made a public announcement that students were not to give any teachers any gifts unless we were going to give all teachers the same gift.

This was obviously a bit of a problem since I couldn’t exactly come back the next day with additional candy bars. So, I marched into her office to address this issue. Upon entering the office, I made a show of opening a chocolate bar and breaking off exactly one piece and placing it on her desk. I told her that I was going to give her a full candy bar, but I now had to share her chocolate bar with other teachers that I didn’t really care so much about anyways.

That rule was quietly lifted.

Breaking the Rules Facts Pikrepo

34. Hurricane Hugo

In 11th grade, now 30 years ago, we were told to use Memorial Day as a weather make up day from Hurricane Hugo. Us students, and many teachers, felt this was disrespectful and suggested to just add the day to the end of the school year. The state insisted. Very few people showed up for school including me, my brother, and most of the faculty.

Toni Morrison FactsMax Pixel

35. Summer School

My brother missed enough school during the year that the school required he attend summer school.

The penalty for not attending summer school? You'd be kicked out of summer school. So, he never went. And they didn't hold him back, because he knew all the material.

Class Clown Stories factsShutterstock

36.  Power Struggle

I had a teacher who got into a power struggle with every reasonably smart kid, so we tended not to try in her class. As a result, she began to grade the progress monitoring tool we used. This proved to me that the tool didn't matter; if it did, she would have graded it from the start instead of waiting until she realized she looked bad. So, I began to fail every test I took on the platform.

She was really angry at me and told me to call my parents. But, my parents backed me because choosing to fail is not a violation of any rule.

Teachers Cheaters FactsWikipedia

37. Standing Ovation

There was a presentation on vaping last year by some poor woman from an advocacy group or something. After every sentence, or whenever she paused, the whole assembly (all 300 kids in my grade) would give a massive standing ovation. We weren’t stopped until we had done it like 15 times.

Gary Oldman FactsShutterstock

38. Look Good in Plaid

There was blistering heat to the point of people passing out, yet we were all forced to wear black trousers. We were dying of the heart and a guy comes in in shorts. He gets sent home only to return after reading the school rules on uniform. He is in a school-colors plaid skirt…legendary.

Breaking the Rules FactsFlickr,m01229


39. Underwear and a Tie

Not me but my friend’s dad—so, a good 50 years ago. His teacher told him his tie was the most important part of the uniform and he had to wear it no matter what. That lunchtime he gathered half his school year and the next day, about 100 people turned up wearing nothing but underwear and a tie.

Breaking the Rules FactsShutterstock

40. Beard Badge

A guy I know ran a campaign to lift my old high school's strict policy on facial hair. The policy was to have none unless religiously exempt—they gave you a card for that, I believe it was called the beard badge. He refused to shave and had a banner and shirts made that said, "With a great beard comes great responsibility".

Attila The Hun FactsShutterstock

41. Butts on Campus

At my middle school, you weren't allowed to use phones on campus, including after school. A lot of my friends and I had no choice but to stay late after school, so we asked our security guards if we could use our phones. His answer was, "As long as your butt is on this campus, you can't use your phones until after 4:00".

We also had a rule saying that once you left campus, you couldn’t come back without a reason (like an extracurricular activity). Lucky for us, there was a sidewalk right outside the school that we could sit on while still having our feet on the campus. So, we would sit our butts down on the sidewalk and still be on campus. We could use our phones and we could still stay at school.

Breaking the Rules FactsPxHere

42. Better Grades

Someone stole a key from the janitor, as he just left them on his desk. It happened to be a universal key to all the locks, except for the server room. The server room had a second hidden door, which they found. They came in after school and stole the servers from the school. All the grades and data for the students were on those servers.

The teachers had to figure out how to recreate all the student's grades, which honestly, they did poorly. Pretty much everyone passed every class, you could just argue for a better grade.

Breaking the Rules FactsShutterstock

43. Shirt On, Shirt Off

I used to wear those sarcastic shirts with dumb saying in them. Example: “I get your point but still think you’re stupid". I was taking weightlifting during my senior year. Of course, I thought I was getting ripped and looked good. Anyway, class is over I get changed head out to the hall waiting for the bell. One of the older history teachers comes out. I don’t remember his name.

He sees me, reads my shirt and yells, “That’s disrespectful, take it off". Right then the bell rang. I yelled back, “Okay!” I take my shirt off and walk to my next class, which was English. The English teacher was new and I may have had a crush on her. Everyone is coming in looking at me weirdly. The teacher walks up to the front of the class finally sees me.

She was one of the few teachers who actually liked me. She just gives me a super puzzled look. She asked why I didn’t have a shirt on and to put a shirt on. I put my shirt on and tell her the story. She is just shaking her head. She ended up talking to the teacher who told me to take it off. He was furious. But, he didn’t know my name so I didn’t get in any trouble.

Justin Trudeau FactsShutterstock

44. New Sweaters

We weren't allowed to wear sweaters that weren't from school. This rule was never really enforced but they had just come out with a new sweater design after like 20 years of not having one. They wanted to get all the money from the students they could. I came up with an ingenious plan. Like a good student, I started going to school with the school sweater—one from 20 years ago that I found in my dad's closet.

There were many confused faces in the principal's office that day, but ultimately me and my sweater lost.

Breaking the Rules FactsWikimedia Commons

45. Failed Plan

Our high school wanted us to wear lanyards with a barcode and a mugshot on it around our necks all day. Otherwise, we would get punished. If you forgot yours at home, you had to go to the office and sign in for a loaner lanyard. I organized a strike one day where no one would wear their lanyard in protest. I had a ton of support and a lot of people were down to participate in this peaceful protest.

The day comes and I'm all pumped. I walk into school without my lanyard. Everyone else was wearing their lanyard. The students still wear lanyards to this day.

Breaking the Rules FactsFlickr,Mack Male


46. Different and Proud

Well, I didn't rebel by choice, it was just who I was. My high school was extremely small and conservative. I was the one and only raging liberal who dressed in crazy colors, dyed my hair every shade of the rainbow, and questioned everything obsessively. My views were not appreciated by many. I also happen to be bisexual, which didn't go over well with my Christian classmates.

Overall, I was just different and proud of it.

Breaking the Rules FactsShutterstock

47. Foreman Grill

There was technically no rule against bringing a George Foreman and a cooler of breakfast meats and then cooking it up in study hall. Until that little French teacher of mine stumbled into the back room of the student center to find a half dozen of us enjoying our steak breakfast. He just ruined the whole thing.

Breaking the Rules FactsFlickr,Meal Makeover Moms

48. No Paper

Some dude in my class was caught cheating during an exam. He quickly put the paper on his chair and sat on it, but the teacher was sure he had a paper. Then the teacher asked the dude to stand up, there was nothing on the chair because he was pressing his butt hard enough to grab the paper. The teacher left him alone.

Class Clown Stories factsShutterstock

49. 100 Times

We had an awful Spanish teacher in middle school who collectively punished the class by making us write the same sentence a hundred times over in detention. On one of these occasions, my friend and I asked her if we could type our detention in the computer lab so we could improve our "typing speed". She said yes.

Anyway, we didn't do much typing but did learn how to write a basic program that printed the same line a hundred times over.

Shy kid FactsPixnio

50. All Hats on Deck

We had a rule that no hats were allowed in school. In high school junior year, there was this one kid in my grade that was allowed to wear one, due to him having Alopecia Universalis, which is basically rapid onset hair loss. A new teacher wasn’t aware that he was allowed to and asked him to take it off. The kid explained why he was able to, but the teacher’s reaction was utterly brutal. He didn’t believe the kid, forced him to take it off, and was being very cruel to him for the rest of class.

The next day, everyone wore hats to school as a sort of rebellion against the teacher. She got really mad and started yelling at the students and said some nasty things. She got fired.

Breaking the Rules FactsFlickr,BPS Flickr

Sources:  Reddit,

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