T-shirt printing is an art, not a science — though having said that, there are definitely some hard-and-fast rules for things you really shouldn’t do when it comes to printing your tees. Like, let’s say, making sure your shirt doesn’t suddenly say something vulgar when you fold it up. Or perhaps you’ve intentionally put something vulgar on it in the first place; that’s also a no-go. Other times, it comes down to the wrong person wearing an already questionable tee.

Whatever the case may be, these T-shirt fails are ones we hope to never see again. They say there’s a time and a place for everything, but that doesn’t apply here…

Keep Calm and Try… What?

worst t-shirts

“Keep Calm and Try an Ale”- a cute take on the “Keep Calm and Carry On” trend for a pub. Or, rather, it would have been, except the shirt invited you to try something very, very different from certain angles. We’re guessing they either had a steep decrease in sales — or the exact opposite.

Tough game, I tell you!

worst tees

Did he happen to land on the “Go to Jail” square, by any chance? Not the ideal thing to wear for your mug shot — or is it?

Let’s just hope she doesn’t ask what that means

t-shirt fails

Nothing says “Day out with the family” quite like cunnilingus.  

So you know how we keep talking about this timing thing?

t-shirt printing failures

Yet again, someone sported exactly the wrong tee at the wrong time. Timing, people, timing.

Thin on humour

funny t-shirts

Some people might find it funny to see a man who almost certainly doesn’t restrict his eating wearing a shirt that says “I beat anorexia.” But trivialising a serious illness isn’t a very good joke.

Wasn’t funny the first time

bad t-shirts

It’s 2016. This joke is just sad. Does anyone really still think this kind of stuff is funny?

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Still seen on tourist trap stalls everywhere

FBI t-shirts

There are two takes on this shirt – “FBI = female body inspector” or ‘FBI = federal boob inspector.” Either way, we’ll refer to our previous point on this one.

Justin, is that you?


Unless Justin Bieber secretly joined punk band Black Flag while nobody was paying attention, we’re going to chalk this one up to poor design choices.

Worst knockoff ever

bad bart tee

While Bart does say “eat my shorts” and has a skateboard, that’s about all this tragic garment got right.  If you’re going to do a knockoff, at least get it right.

Who approved this?

too pretty to do homework

“I’m too pretty to do my homework so my brother has to do it for me.” Things didn’t get any better in the product description of the JC Penney garment: “Who has time for homework when there’s a new Justin Bieber album out?” After (justified) widespread outrage, the shirt was discontinued — and someone lost their job.  

Crafty girlfriend

worst printed t-shirts

These shirts were all lovingly hand-crafted by a girl for her boyfriend going on vacation. Lovingly as in the same way Kathy Bates was loving in Misery.

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You don’t have to accept all free T-shirts

free wrong tee

This man (unwittingly?) walked around with a shirt advertising entertainment for grownups. Lesson: just because it’s free doesn’t mean you have to wear it.

It really depends on who’s wearing it…

black woman t-shirt

“Danger: educated black woman.”  There is a customer niche that could pull this one off. But this guy? Definitely not part.

OK for a frat boy…


…but definitely not for children. We’re not sure if this is supposed to be racist or what, but regardless it’s tasteless — just tasteless.

Back to geography class

worst t-shirts

Asia certainly looked different when I was in school. Did Britney Spears happen to draw this map?

No one caught this one? Really?

math t-shirt fail

This isn’t a case of a shirt suddenly appearing vulgar when placed a certain way. Whoever designed it placed the text on purpose— and somehow nobody realised how it would read?

Same hair, I guess?


Yeah, that’s definitely not Nirvana. But any member of Hanson would probably be thrilled to be mistaken for Kurt Cobain.


And that brings us to the end of our list of the biggest T-shirt fails ever. Some people just never seem to learn. If you happen to own one of these T-shirts, go find it and then please proceed directly to the nearest bin. Thank you!

Is there any other T-Shirt fail that should be added to this list? Then please, let us know. Leave us a comment below or send us a message via any of our social media outlets.

In the meantime keep reading the Printsome Blog for more awesome content.

Print on Demand

Here at Printsome, we’ve always supported creative endeavours. Through our print on demand services, we are helping agents, artists, entrepreneurs, designers and content creators who have their own T-shirt line.

With dropshipping we deal with all the inventory and logistics headaches so you have more time to do what you love. We offer very fast dropshipping services in the UK, Europe and the rest of the world.

No matter where you want to sell merchandise on demand. We deliver anywhere.

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If you have any doubt, you can contact us here. Our friendly team of printing advisors will help you. Print on demand worldwide has never been easier!


Jessica freelances Corporate Communications Writing for the Printsome Blog. She goes above and beyond to ensure that we are talking and engaging with customers in just the right way. She is also English Copywriter at eDreams ODIGEO.

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