To Top

These T-Shirt Fails Have Got Us Cringing, But We Can’t Look Away

Updated on

1. Eat your hearts out, ladies. This dude isn’t going to date just any beauty who shows up at his doorstep, and why should he? He cooks, he’s got a handsome ‘stache, and (clearly) a killer sense of fashion.

Hilarious T-Shirt Fails


2. Most won’t look at this guy and see a survivor, someone who powered through hardships when all odds were stacked against him. But you’ve got to give him credit for his personal victory!

Hilarious T-Shirt Fails


3. Someone should swap this little girl’s shirt with something that better reflects her emotions. Why rock a “Super Happy” shirt when you’re having a rotten day? The character on the shirt looks just as perplexed as us.

Hilarious T-Shirt Fails


4. Just keep parading around with that shirt, and kudos on that determination. We’re sure with an outfit like that, eventually, someway, somehow, the right person will “discover” you. That’s how that works, correct?

Hilarious T-Shirt Fails


5. Given that this dude’s rocking a George T-shirt, a George coffee mug and has his TV paused on George, we have a few clues as to who his celebrity crush might be. For the record, we’d be hiding our face too.

Hilarious T-Shirt Fails


6. Meanwhile in coordinated T-shirt fails, this family has no problem publicly embracing their love for their favorite Seinfeld character. Imagine walking by this bold and beautiful bunch, feeling all of those scowling George eyes on you.

Hilarious T-Shirt Fails


7. If there is one thing that this woman doesn’t have time for, it’s “that”. What exactly is “that”? We’re guessing that it can be almost anything. Don’t even ask her for any extra favors, just read her shirt.

Hilarious T-Shirt Fails


8. Holy T-shirt fails, Batman! This poor guy definitely chose the wrong outfit for the occasion. If we had to wager a guess, from the looks of it, he’s probably the only person in the room that would do him.

Hilarious T-Shirt Fails


9. Anyone who grew up in the 1990s is going to remember the D.A.R.E. anti-drug program. This papa bear scrapped the slogan, kept the font, and decided gentleman suitors were more of an issue for his daughter. Careful, guys.

Hilarious T-Shirt Fails


10. There’s got to be a backstory behind this shirt. Perhaps this young lady decided to wear it on her last day of working as a personal trainer. She was fed up with the sweating and crying of her clients.

Funny Shirt


11. Her shirt says it all. She’s got lovely red hair, and she’s most clearly down to her last…care. It’s the perfect get-up for chilling all alone at your local Chuck E. Cheese.

Hilarious T-Shirt Fails


12. Can this really be counted as a T-shirt fail? Seriously, if anyone is planning to take her out, they’d better be prepared to shell out some big bucks. We’re talking Saturday nights at the Sizzler, people!

Hilarious T-Shirt Fails


13. Come on, dudes, don’t go getting offended now. Who needs a guy when you can just acquire a ton of sassy cats? You’ll feed them, clean after them, and maybe you can even pet them — if they feel like it.

Hilarious T-Shirt Fails


14. Shall we count this among the T-shirt fails, or T-shirt wins? After all, much-beloved Jeff Goldblum is finally getting the respect he deserves. When you see someone sporting this steamy getup, you know you’ve met someone special.

Hilarious T-Shirt Fails


15. It seems T-shirt fails and painful puns go together like peanut butter and jelly. Seriously, even the mere idea of a lake or restaurant being hard of herring is any fish lover’s worst nightmare. Yuck!

Hilarious T-Shirt Fails


16. Of all the T-shirt fails out there, this one offers a challenge. No doubt some dumb dudes are going to see this message and wonder what exactly happens if they unlock the shirt. Keep your hands to yourselves!

Hilarious T-Shirt Fails


17. Now, we certainly can’t deny this shirt’s message. Glue used that way definitely won’t keep families together. But it’s all a manner of perspective. After all, if properly applied, glue could also keep families together — literally.

Hilarious T-Shirt Fails


18. We all know that unfortunately, there’s a considerable amount of guys around who might take this shirt’s cheeky invitation to heart. One has to wonder how many guys scoured the room before sidling on over.

t-shirt fails


19. Perhaps no shirt has better captured the three facial expressions that define the true range of actor Nicolas Cage. If you’re going to be flaunting the T-shirt fails in your wardrobe, you might as well do it with an Oscar-winner, no?

Hilarious T-Shirt Fails


20. There’s literally no way this guy could have known that morning that he was putting on the perfect shirt for the day’s events. While he isn’t saying much while getting arrested, his shirt is saying it all.

Hilarious T-Shirt Fails


21. Wherever he goes, Michael Jordan is always perfectly dressed. He knew he was going to play beer pong that day and truly rose to the occasion. Any bets on whether he’ll win this game?

Hilarious T-Shirt Fails


22. How many guys are going to see this woman’s shirt at the bar and start treating her to a round? If your life goals include getting some free drinks, even a T-shirt fail like this might work in your favor.

Hilarious T-Shirt Fails


23. Come on, guy. That mustache is not that impressive. And even if we believe your claim that it brings all the girls to the yard, what do you do with them afterwards? We’re hoping it’s a spirited game of lawn bowling.

Hilarious T-Shirt Fails


24. This shirt is a good warning. Whatever you do, don’t mess with this guy, don’t look him in the eye for too long, and if he enters a room, get comfortable somewhere on the other side of the room.

Hilarious T-Shirt Fails


25. Sure, you aren’t going to date this woman without stepping on a few Legos in the middle of the night and spending time with that crying child who will likely dislike you. But don’t give up just yet!

Hilarious T-Shirt Fails


Sources: Instagram, Reddit, Facebook

More from IcePop

More in OMG!