Shirt Puns
1. I ordered a new shirt online but when it arrived, it was too big. What a waist!
2. I was looking for a new shirt to wear to work but couldn’t find any I liked. I guess I’ll just have to make dew.
3. My friend was bragging about his expensive new silk shirt. I told him not to get too cocky about it.
4. I spilled coffee all over my favorite work shirt. It left a big stain which ruined my outfit. I guess that’s just my cup of tea.
5. I’m thinking of starting a business selling custom shirts. I’ll call it “Dress for Success” because my shirts will really suit people.
6. My wife threw out my old holey shirt. I’ll miss it – it was holy to me!
7. I bought a new Hawaiian shirt covered in pineapples. It wasn’t very appealing.
8. I was shopping for a new dress shirt but couldn’t find my size anywhere. The search continues!
9. I ordered a shirt with a company logo embroidered on the pocket. Let’s just say it wasn’t my best branding decision.
10. My friend’s shirt was missing a button so he replaced it with one shaped like a cat’s face. I guess you could say he had a purr-fect solution!
Shirt One-Liners
11. This new shirt has more wrinkles than my grandpa!
12. I ordered the wrong size shirt – next time I’ll have to take better measurements.
13. Don’t iron while wearing your shirt, unless you want to feel the heat!
14. My shirt used to be white before I washed it with that red sock.
15. This shirt is so bright it ought to come with a warning label.
16. I’m not superstitious, but I won’t wear this shirt on days that I have exams.
17. My favorite shirt shrank in the wash, guess I can give it to my kid now.
18. This shirt makes me look like I’m back in the 80’s…and not in a good way!
19. I ordered the wrong color shirt online – I guess that’s my faux pas for today.
20. It was hard ironing all the pleats on this formal shirt – my arm is still sore!
Best Shirt Jokes
21. I was running late for work when I realized my shirt was inside out. I guess you could say I was not having the best start to my day.
22. My friend bought a vintage Hawaiian shirt covered in flamingos online. Let’s just say when it arrived, it wasn’t quite as “vintage” as he expected.
23. I was wearing my nicest silk shirt on a first date when the waiter spilled red wine all over me. My date said I looked like I got stabbed! Not the vibe I was going for.
24. Someone spilled coffee on my white shirt right before an important presentation. I had to give the whole speech with a big brown stain front and center. So embarrassing!
25. I was running late to work when I realized my shirt was not only inside out but also backwards. Let’s just say my coworkers got a good laugh at my expense.
26. My husband shrunk my favorite shirt in the dryer. When I confronted him, he said “Honey, maybe it’s less that the shirt shrunk and more that you expanded?” Sleeping on the couch it is!
27. I spilled pasta sauce on a brand new white shirt 5 minutes before a job interview. I had to do the whole thing with a big orange blotch on my front. Pretty sure that impacted my chances!
28. My friend bought a shirt with a joke on it but didn’t realize it had a dirty second meaning. Let’s just say he got some interesting reactions wearing it around town!
29. I ordered a fun loud floral Hawaiian shirt for vacation. My wife took one look at it and said “over my dead body are you wearing that in public!” Marriage is all about compromise, right?
30. I was in a rush and absentmindedly buttoned my shirt all wrong. Didn’t realize it till I got to work and saw my lopsided buttons in the bathroom mirror. That was an awkward first hour on the job!
31. I spilled red wine on my date’s new white shirt and then tried to help by blotting it with my napkin. Ended up just making the stain bigger! Safe to say that was our first and last date.
32. My mom accidentally bleached a pink stain onto my favorite work shirt. Tried to hide it with a sweater but my coworkers still asked if I “felt pretty in pink” all day long.
33. I was running late and put on a wrinkled shirt straight from the laundry basket. My boss took one look at me and said “Long night?” Guess I won’t be doing that again!
34. I spilled coffee down the front of a new light blue dress shirt on the way to an interview. Tried to cover it up by buttoning my suit jacket but the interviewer definitely noticed. I didn’t end up getting the job – probably thanks to my “coffee camouflage” fail!
35. My friend bought a vintage band t-shirt online that turned out to be a cheap knock-off. Let’s just say the botched lyrics gave it away pretty quick!
36. I spilled grease on my favorite going-out shirt while cooking breakfast. The stain didn’t come out no matter how hard I scrubbed – and neither did the smell! Had to throw it out completely.
37. My mom shrunk my favorite college t-shirt so much in the wash that it could fit my dog better than me. RIP to the greatest shirt I’ve ever owned.
38. I was in a rush and didn’t realize my shirt was inside out when I showed up to a big meeting. My coworkers politely avoided making eye contact for the rest of the day!
39. I wore a new work shirt without washing it first and got horrible hives from the chemicals. Had to call out sick from the itching – not my smartest fashion choice!
40. I spilled red sauce on my shirt right before taking a group photo. When the pic came back, it literally looked like I’d been shot in the chest!
41. I was running late and grabbed a wrinkled shirt out of the laundry basket to wear. My girlfriend took one look at me and said “did you sleep in that?” Ouch.
42. My mom shrunk my favorite band tee so small in the wash that my little sister fits in it better than me now. Heartbroken doesn’t even begin to describe it!
43. I spilled coffee down a brand new light blue dress shirt on the way to a job interview. Tried hiding it by buttoning my suit jacket but the interviewer definitely noticed.
44. I grabbed a shirt from the back of my closet to wear on a first date and didn’t realize it had a huge hole in the armpit. Let’s just say my date got an eyeful!
45. I spilled spaghetti sauce on my new white shirt right before taking photos for a dating app. Had to scrub furiously just to make myself presentable enough for a first impression!
46. My boyfriend shrunk my favorite tee in the dryer despite me telling him not to. Now it fits my dog better than me – he’s in the dog house for sure!
47. I spilled coffee on a light shirt on the way to work and tried covering it up by buttoning my sweater over it. My boss told me she liked my “modern art.” Doh!
48. My mom accidentally bleached a big splotch onto my work shirt. Tried covering it with a scarf but my coworkers still asked if I was trying to make a “bold fashion statement.”
49. I spilled pasta sauce on a brand new white shirt right before a job interview. Spent the whole time worried the interviewer was staring at the big orange stain!
50. I was in a rush and didn’t realize my shirt was inside out when I ran into my crush at the coffee shop. So much for trying to make a good impression!
51. I spilled coffee on my light blue shirt on the way to see my girlfriend’s parents for the first time. Her dad said, “starting early today, huh?” Face palm.
52. I wore a new work shirt without washing it first and broke out in itchy hives from the chemicals. Had to call out sick and explain my “fabric fail” to my angry boss.
53. I spilled pasta sauce on my favorite shirt right before date night with my wife. Had to endure her sarcastic comments about my “decorative splatter design” all evening long.
54. I accidentally wore two different shoes and had my shirt on inside out on picture day at school. Let’s just say that yearbook photo haunts me to this day!
55. I spilled red wine on my date’s brand new white shirt and tried to blot it with my napkin, which only made it worse. Suffice to say, it was our first and last outing!
56. My mom shrunk my favorite tee with rude graphics on it in the wash. Now my 8 year old sister wears it thinking it’s so cool. Awkward!
57. I spilled coffee on my shirt on the way to my high school reunion and walked around with a giant stain all night. So much for trying to impress my old classmates!
58. I grabbed a wrinkled shirt from the laundry basket for a first date and my date asked if I “got dressed in the dark.” I didn’t get a second date.
59. I spilled pasta sauce on my brand new shirt right before taking my online dating profile pic. I ended up having to retake it because I looked like a slob!
60. I spilled red wine down the front of my shirt on a first date. Then I excused myself and never came back from the bathroom. Ghosted for life!