Hilarious T-Shirt Fails That Prove Fashion Isn't Only For The Trendy

LOL July 17, 2018 By Hugo

Have you ever passed someone wearing a T-shirt that was so funny/cringeworthy it almost made you die from laughter? From witty captions and hot people wearing eye-catching shirts to tourists not knowing the meaning behind the text, we've come up with the ultimate gallery of T-shirt fails that will have you laughing all day long.


1. The iPood: Coming Soon To An Expensive Store Near You

YouTube/ billschannel

Walk into any electronics department nowadays, and you'll most likely come across a series of "i" products. iPhones. iMacs. iPods. However, it's unlikely you're going to find and iPoo anytime soon unless of course, you buy the T-shirt, rumored to be retailing at $599. 

2. Oh, the irony...

YouTube/ billschannel

If you're overweight and want to embrace it, then do what this guy did and buy a hilarious T-shirt. Obesity is a big problem, but whether you're trying to lose the weight or simply feel comfortable in your own skin, owning your so-called imperfections can sometimes be the best way to combat the haters. Rock on dude!

3.  The Aptest Shirt Ever?

YouTube/ bills chanell

This guy can't have been dumb enough to deliberately get arretsed just so he could have an apt photo opportunity, could he? Well, the Internet makes you do dumb stuff. Let's just hope he got a get out of jail free card before shower time..

4. The Most Understanding Baby Ever?


YouTube/ billschannel


As the shirt suggests, Mummy tore herself to pieces, almost literally, to give life to this little one, so it's good to know that her pain and struggle was recognized. Well, until it becomes a teenager and turns into an ungrateful douche. 

5. Does He Have A Death Wish?!

YouTube/ billschannel

Homeland Security conventions aren't the best place for jokes, and considering how gun-obsessed Americans are, this daring joker was fortunate not to be mistaken for a white member of Isis.

6. When Your Grandma Doesn't Give A Damn

YouTube./ billschanell

If my grandmother set eyes on this T-shirt, she'd have a breakdown and curse the crude words on display, so full props for this old lady for being herself!

7. When Cake Is Life

YouTube/ billschannel

Most women will accept a drink in a clammy club full of guys, but this woman will happily do anything if a slice of sugary goodness comes her way. Perfect, then, for the main course of something a lot saltier.

8. Make Sure You Understand A Bit Of The Language

YouTube/ SC Videos

Many Asian tourists love buying English T-shirts with- what they think- cool imagery and words on them, but little do they know that many designers have cottoned onto this and designed shirts with chucklesome words on them.  And yes, that includes the word fart. What a world we live in!

9. We Both Love Cock!

YouTube/ SC Videos

Asians love British and American culture, don't they? The films, the tv shows, the fashion.. Maybe they should rethink their preferences for the latter, however, and adopt a more neutral fashion tone when it comes to wearing foreign clothes.

10. Preach It, Brother!

YouTube/ RC List

There's hope for the less well-endowed after all as size isn't everything. Well, unless you're married to her. She clearly wishes her man had a bigger...

11. A Better Bush

YouTube/ RC List

President George W.Bush wasn't exactly the most popular President Americans have had to endure, but as is the mighty wit of the Americans, they still managed to make fun of a bad situation. 

12. Telling Cameras How We Really Feel

YouTube/ The Bro Bunker

And the prize for wittiest T-shirt caption goes to whoever this guy is. We can't see him, of course, seeing as cameras like the chop peoples' heads off. 

13. When You're Too Honest

YouTube/ The Bro Bunker

This is one creepy look! If there's any advice this site can give men, it's to not look at a woman like this, least of all when you're wearing that shirt! But hey, it's funny as hell, so at least he's doing something right.

14. She Might Want ToStay Clear Of The Last Guy...

YouTube/ The Bro Bunker

If you're going to wear this T-shirt sweetie, make sure you're not in proximity to guys clad in shirts telling you to drink loads. Just a thought...

15. Honesty Is The Best Policy

YouTube/ The Bro Bunker

We all do it; even YOU. So we should all embrace this man and hug him for being so honest. If only there were more people like this brilliant man in the world. 

16. Polish model Natalia Siwiec watches soccer in the most revealing t-shirt ever


Just when you thought the soccer couldn't get any more interesting, up pops this striking beauty on the tv screens at the European Championships in 2012. Unsurprisingly, the photos of a scantily clad Siwiec attending her country's matches led many to label her "Miss Euro 2012". 

17. Distracting the male fans (and possibly the players)


An Albanian soccer fan leaves little to the imagination in a two-strap item that is deliberately one size too small for her! Team USA, take note: If you want more dudes to watch the male team, then try and draft in some fans who look like this!

18. Does she know who the real number 10 is?


The World Cup unites soccer fans in a way no other tournament does, and that includes women who wouldn't normally watch the Beautiful Game! Just take this insanley attractive woman. While she might not be a soccer-mad fan or know who Poland's number 10, Grzegorz Krychowiak, actually is, she looks great and epitomizes all that is good about the sport of soccer!

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