As we grow older, it’s easy to end up out of the loop on style choices. We see it first with our parents. Then, one day, it’s us too. It often means we dress in clothes that are completely inappropriate for our age.
Sometimes it happens completely by accident. Other times, it’s a result of trying to be funny. However, for most of the people on this list, they are simply oblivious. That is the only way we can explain the ridiculous clothing items that they were caught wearing.
From offensive t-shirts that are demeaning to whole populations of people to jokes that are downright raunchy, these 40 people run the gamut. It begs the question, who bought them these hilarious outfits and do they even understand what they mean? That’s what we’re trying to figure out.
For starters, we find it hard to believe that this elderly woman even knows what a hipster is. Secondly, wearing a t-shirt like this actually might even make her a hipster herself. It certainly isn’t a mainstream outfit.
Maybe his name is Dick? That is the only way to explain this ridiculous sweater choice. Otherwise, there is no way he would ever wear such a thing.
Her yellow sweater has a very simple message — “I hate everyone”. Although, her happy and smiling face conveys a different message. At this point, we don’t know what to believe.
He’s definitely not the number one eligible bachelor in the city. However, he is willing and able. If you need to kill some time, he’s totally down for a romp or two.
It looked like such a cute scarf to wear. It was green, just like the color of nature, and had images of plants on it. Unfortunately, she had no idea what type of plants they were…
Someone needs to teach this guy that being sexy isn’t about making sex jokes. If he thinks he has any chance in the dating market wearing a t-shirt like this, he better think again. No girl is going to fall for that.
This guy’s t-shirt is actually pretty funny. He knows he isn’t in the best shape and isn’t afraid to let people know. If you are behind him in the marathon, you better have a good excuse.
We love the shirt this woman picked up on her Key West, Florida vacation. She sure knows how to have fun. She wears the “old shirt” proudly, with a beer in her hand and a smirk on her face.
It’s important to keep clean while cooking. That’s where aprons come into play. The design and pattern are not important, as long as it prevents spills from staining your nice clothes underneath.
Visa is accepted everywhere. However, this Asian man accepts vagina as a form of payment too. It’s pretty offensive. We wonder if he actually understands what that word means.
At first, you might be tempted to make fun of this man for his pink shirt. Although, once you read it, you’ll be eating your words. He is very good friends with your girlfriend.
This man’s appetite is on display for the whole restaurant to see. Although, it’s not food that he is craving. His appreciation is more for the finer things in life.
This man is willing to do whatever it takes to earn a buck. There is nothing that is beneath him. After all, twenty dollars is twenty dollars.
This guy’s t-shirt includes lyrics from a song by rapper Kendrick Lamar. It’s not what you would expect a man of his age to be wearing. However, hip hop is what he vibes with.
Here we have another elderly individual who is down with hip hop culture. She is a huge gangster. You had better think twice before you step to her and her crew.
Not all old people are technology-illiterate. This guy is definitely up to speed. He knows all of the best online streaming websites and is even willing to advertise them.
The joke starts out pretty innocently. A man walks into a bar with a monkey. However, soon after, the joke takes a turn for the worst…
You might not be able to guess it just by looking at this man, but he’s a lesbian. At least, that is what his shirt says. Whether you believe him or not is up to you.
Don’t worry, she’s not 100% hotter than you, only 20%. It’s a number that’s easy to digest. On a scale of 1 to 10, it’s only two points higher than your position.
His new swag is pretty awesome. He does his best to stay up to date on the latest trends. Between the shirt, the LED belt buckle, and his studded jeans, he’s got all of the bases covered.
There is definitely some truth to the statement on this man’s shirt. It’s pretty funny. However, the better option would probably be neither of the two choices.
The stain on the carpet is worse than we thought. It’s not just one man’s bodily fluid, but a group of several men’s bodily fluids. Really, we wonder if this guy has ever actually Googled bukkake before to see what it means…
Cocaine and caviar is a great combo. At least according to several hip hop songs that we’ve listened to. We’ve never tried the combo personally, but this woman is all about it.
Here we have another hilarious bukkake reference. We’re warning you, don’t Google the term. If you don’t know what it means, just move along and forget about it.
There are some major benefits to being bald. For example, the amount of sunlight you receive. When your hair is looking patchy, a few minutes outside is all it takes to charge up your vitamin D levels.
That is one insane and heavy-looking weapon. It’s the hammer of the Norse god, Thor. It’s great for anarchists like this man who love freaking out and breaking things.
27. Becoming Grandparents
Just because you get old doesn’t mean that you have to give up your sex life. In fact, once you reach a certain age, you automatically get invited to all sorts of fun new clubs. It happens by default.
She is probably curious as to why the strange woman wants to take a picture with her. After all, she thinks her outfit is very normal. However, the truth is that her clothing choices are simply one of a kind.
This nun is definitely a little more rebellious than most of her peers, but who cares? Yes, she has been bad, but she is still a complete saint compared to almost everyone else in the general population.
Here we have another man with a wise saying on his t-shirt. It’s true, if you are heavier, it’s harder to be kidnapped. Eating yourself to obesity is just smart thinking.
We don’t even know what to think about this one. Let’s just hope that the shirt is thirty or forty years old. If it was bought recently, then it is slightly bizarre.
This guy isn’t that old yet, so we’re not sure what his excuse is. He likely thinks that his t-shirt is pretty funny. However, if this is what he is wearing now, we can only imagine what he’ll be wearing down the road.
The real star of this photo is the man standing on the left in the back. The upwards-facing arrow points to Mr. Right, while the downward one points to Mr. All Night. At least, that is what he thinks…
“I don’t smoke crack, I lick it,” the t-shirt reads. Which crack in particular? We’re not sure. We don’t even want to speculate as to what his dirty mind is thinking about.
Being unemployed is never fun. Common wisdom says to take whatever job you can get, any job. Although, there are some boundaries that one probably shouldn’t cross…
This woman couldn’t care less what her t-shirt says. A shirt is a shirt. It’s for wearing and the saying on the front of it is completely irrelevant.
He needed to go shopping and grabbed the only bag that he could find. The message doesn’t really match his personality. However, it does work for carrying stuff, so it’s whatever.
We wonder what his wife thinks of his raunchy t-shirt? It is essentially porn. If we were related to this guy, we would refuse to be seen in public with him.
All we have to say to this man is congratulations! He pooped today. It is a big accomplishment that is definitely worthy of a celebration.
You can be anything you want when you grow up. It’s a common thing that parents say to their kids. However, when they say “anything”, it’s normally implied that they are referring to actual jobs.
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As we grow older, it’s easy to end up out of the loop on style choices. We see it first with our parents. Then, one day, it’s us too. It often means we dress in clothes that are completely inappropriate for our age.
Sometimes it happens completely by accident. Other times, it’s a result of trying to be funny. However, for most of the people on this list, they are simply oblivious. That is the only way we can explain the ridiculous clothing items that they were caught wearing.
From offensive t-shirts that are demeaning to whole populations of people to jokes that are downright raunchy, these 40 people run the gamut. It begs the question, who bought them these hilarious outfits and do they even understand what they mean? That’s what we’re trying to figure out.
