Trolling Your Boss Is Fun, Especially When They’re Helpless To Stop You (15 Stories)

Working from home during quarantine means you can basically wear what you want. Bathrobe? Sure. Fancy shirt over sweatpants with holes in them? Go on. Underwear? Just make sure your Zoom camera is off.

But for some folks like this poster from Reddit, work attire is perhaps taken too seriously. 

“Little background story. My boss is a huge douche. All he does all day long is walk around and make sure everyone has their shirt tucked in,” the OP starts. Well, on the OP’s birthday, he comes into work and is greeted by coworkers telling him Happy Birthday. His boss? Walks on over and tells him to tuck in his shirt. No Happy Birthday recognition or anything. 

“So I say, ‘ok no prob, I just have to put my stuff down real quick and I’ll take care of it.’ So I walk over to my desk, which takes approx. 7 seconds to get to. I go to put my stuff down, and as I am he comes up behind me again and says, ‘I said to tuck in your shirt!'” 

Annoyed, the OP busted out the HR manual to check the rule on tucked-in shirts. 

“Turns out you must tuck in all shirts EXCEPT a Hawaiian shirt or a ‘Guayabera’ shirt. So I take my ass to Wal-mart, and buy 10 of those f—rs, and wear the most obnoxious Hawaiian looking shirt the next day. The second I walked in, he looked me up and down, glared, turned around and walked away. When everyone asked why I was wearing such a ridiculous shirt, I told them about the loophole, and now half my office is wearing Hawaiian shirts, and it’s driving my boss crazy.” 

The OP’s question to Reddit? What ways have you been able to stick it to the man by playing by their rules?

1. 

“A couple of friends of mine work at Wal-Mart. They found out that kilts are well within the dress code as long as they are the correct color. Drove their managers nuts. It’s been a year and absolutely no problems though.” — SergeantKoopa

2. 

“While I was in the Navy it was recommended that I get an extensive surgery on my ankle. My command felt that I “didn’t deserve a bunch of time off for a surgery” so they said they would approve it but none of the convalescent leave. They refused to sign ANY paperwork. First thing I did was hit them with the regulation stating that they were required to respond to all requests within a certain amount of time (3 days I think). They responded with a ‘no.’ So then I had Navy legal draw up paperwork (with accordance to regulations) that my command would be responsible for 100% of my medical care if they did not abide by doctors orders. I then let them know that would mean that ALL of my medical care would then be handled by civilians and the command would be responsible for paying the bill out of their budget. They approved my surgery, convalescent leave, and convalescent leave extension.” — [deleted]

3. 

“Used to work at a TV station. Absolutely awful management and horrible bosses. Complained about it to friends all the time. Some would even ask me on facebook about my job and I would reply- but I knew I could get fired for speaking ill of the company. So I read the HR Handbook and found out as long as I don’t specifically name the company, I can’t be fired for it. So, about a month later, I realize I can’t take this shit anymore and post on facebook how terrible my job is, never mentioning the company by name. They fire me a day later, I gladly walk out of that building and into a lawyer’s office- got $17,800-my yearly salary (seriously).” — risto1116

4. 

“Worked in one corporate kitchen where our GM didn’t like our music so he would put on children’s music, so we all started singing a long at the top of our lungs…We won that war of attrition. Years later in another kitchen we had surround sound in a closed kitchen where the uppity GM did not like our music and started passing draconian censorship rules about the music…so we switched it to children’s music for a week. Moral of the story: never underestimate the power of a kitchen crew of misfits singing “banana phone” at the top of their lungs to fight fascism, motherf—r! Viva La Raffi! Viva La Raffi!” — sith6six

5. 

“My boss went away for about 3-4 weeks for a conference, and while he was away, a workmate and I had an idea… a George Foreman grill, and then we’d go to the deli and grab stuff for lunch: hamburgers, lamb chops, pork, steaks etc. We did this every day for over a month, and when the boss got back he put a stop to it, with the exact words ‘I don’t want that thing inside the office.’ So we took it to the shared kitchen area on our floor (We rented a suite). When he got angry at that, and said, ‘I DONT WANT IT ON THIS FLOOR,’ we took it down to the underground parking area and used the power outlet at his parking space while he was out at lunch. He caught us because he was coming back from lunch with a business partner (in the car with him) and we were hunched over a tiny George Foreman grill making hamburger patties. Imagine 3 IT guys, crouching on the ground like cavemen, in a poorly lit underground parking lot, cooking hamburger on the concrete floor. Yeah, it went over about as well as you would think.” — UNREASONABLEMAN

6. 

“Back when I was working and attending classes I would go straight from campus to work, getting me there anywhere from 10-20 minutes early before my shift. On occasion my boss would ask me to help him out with something before I clock on, putting something away or answering the phone. Over the span of a couple months, this evolved from ‘occasionally’ to ‘every day your shift starts when you get here.’ After doing this for a couple weeks (still clocking in at my usual 3pm) I decide that if I’m working for a few extra minutes each day, I’m gonna get paid for it. I did this ONCE, and I didn’t make it an hour into my shift before my boss is screaming at me and throwing down the employee handbook saying that I’m only allowed to clock in 5 minutes before and after my scheduled shift. Needless to say, I made it a point to not check in until 5 minutes after my scheduled shift every day, no matter how early I was. Fast forward 3 months and my boss gets fired. He got what was coming to him.” — GrandOak

7. 

“My father was working in a post office in the early 80’s. It was an unusually hot day with ~85°F inside. There were no fans available so it was crazy. Men weren’t allowed to wear shorts, but dad came to work wearing shorts which covered his knees and a part of his shin, figuring he was fine. He wasn’t, and his boss sent him home to change. He returned in his grandfather’s bonjour from the late 19th century. Top hat and all. The boss kept asking if it wasn’t a little hot in that suit but he said he was fine.” — chappe

8. 

“Not work but school. I’m a senior in high school, and one day a bunch of senior guys decided to start up ‘tank top Tuesday’ every Tuesday about 1/2 the senior guys would come to school in a tank top. Our school had no rule about tank tops except that the straps be at least two inches thick so we didn’t anticipate any problem, especially considering girls at our school wore tank tops all the time. After the first day, the school announced that boys were no longer allowed to wear tank tops, when questioned as to why, they claimed that visible armpit hair was a distraction that inhibited learning. The following Tuesday, we all went to school wearing tank tops and sporting shaved armpits.” — Sabrey

9. 

“Not work related, but school. In HS I wore a freecondoms.com t-shirt to school. I was called down to the principals office after 3-4 hours(my cool teachers thought it was awesome in the AM classes) and was told I was promoting abhorrent behavior. I posited that I was in fact trying to prevent unwanted pregnancies. I lost my fight and was told I had to leave if I did not have another shirt. Rather than leaving I put a sticky note over the ‘m’ in condoms and spent the rest of the day harassing faculty about fantastic lakeside condos that I was giving away for free.” — tehpopa

10. 

“When Circuit City was still in business I worked in the warehouse. For whatever reason, they had a strict dress policy of khaki pants, this awful collar shirt that also had to be tucked in. This went for everyone, even warehouse. I discovered through an old warehouse employee guide (Shoved in a draw years ago and forgotten about) That as long as Warehouse employees had khaki colored shorts, with no cargo pockets, and a t shirt with a Circuit City logo there would be no problem. Circuit City stopped making Circuit City t shirts long before I started, but thanks to a local Salvation Army, I was able to pick up, two Circuit City T shirts, and a quick trip to Target for some shorts, and my new uniform was set. My mangers were not happy about my appearance, claiming I looked sloppy and unkempt.” — [deleted]