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It started as a practical way to make union suits more comfortable for those working in hot environments. Then, it was standardized as a part of military uniform and a few decades later popularized by Marlon Brando. Nowadays, it’s at a forefront of fashion runways and picket lines. The humble T-shirt is everywhere. In fact, there’s a high chance you’re wearing one right now.

There’s also a high chance that what you’re wearing is not nearly as bold as the tees on this list. Collected from Instagram account Good Shirts where you can purchase the hilarious masterpieces, these T-Shirts are attention-grabbing to say the least. Scroll down to see which one you would dare to wear.

#1

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Speaking about daring and t-shirts, one would be sorry not to mention the “D.A.R.E. to keep kids off drugs” shirt that became popular in the 80’s. The shirt was produced as a part of Drug Abuse Resistance Education or DARE program that was launched to educate children about the horridness of drug use.

Because the creators of the program tried to appeal to youthful audiences, they poured a lot of effort into making the program look cool. They made t-shirts that looked grunge and asked policemen to come to schools with confiscated cars to give lectures about how drugs can cost you your whole lives.

#2

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#3

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Unfortunately, the branding really backfired.

Instead of making the program fun and exciting, it made drugs look cool. The young people loved the fancy cars the policemen turned up with at their schools; it showed them how fancy drug dealers live. Even the slogan was completely unfitting, with many ironically using it to dare others to use drugs.

The effectiveness of the program that ended up costing somewhere between 200 million and 2 billion dollars was also analyzed by multiple studies, which proved its lack of impact. What has made an impact, though, is the T-shirt, its design popular up to this day.

#4

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#5

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#6

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Another graphic shirt that’s gotten so popular it has lost its meaning is the Che Guevara T-shirt. The portrait of the handsome revolutionary has found itself on all sort of garments that have been sold everywhere from Urban Outfitters, to Vans, to Louis Vuitton. The mass for-profit use of the image is quite ironic knowing that the man in the picture fought for communism.

#7

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#8

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#9

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The legendary Che Guevara’s picture, known as Guerrillero Heroico, was first published in 1967 in Paris Match, the same year that he lost his life. Artist Jim Fitzpatrick was moved by this loss and created the now well-known interpretation of the image as a form of protest.

#10

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#11

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#12

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Soon enough, it found itself in galleries and picket lines, growing more and more popular every day. Eventually, over the years, the image got so wide-spread it lost its meaning. Nowadays, you can spot people casually wearing it on the streets, without giving it a second thought.

#13

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#14

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#15

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Back in 2012, The Human Rights Foundation published an open letter addressing the popularity of Che Guevara’s image. They called attention to the atrocities of the regime and the abuse Che Guevara himself has inflicted upon others. They urged people to ditch the romanticized version of the man and educate themselves on his behavior.

#16

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#17

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#18

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Fortunately, not all popular t-shirts are so overused they get misinterpreted. The legendary “I [heart] NY” T-shirt is still as loved as it’s ever been. Sure, native New Yorkers might see it as a cheesy or touristy thing to do, but that hasn’t stopped modern-day style influencers from wearing them.

#19

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#20

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#21

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The design for the famous logo that appeared in 1977 was born in the mind of Milton Glaser, a famous American graphic designer. He was working on the marketing campaign for the New York State, that was back then going through a rough time with billion-dollar deficit and crime on the rise. The task was to repair the failing image and boost the state’s tourism.

#22

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#23

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#24

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Glaser came up with the design while in the back of a taxi. He sketched the logo on a scrap paper with a red crayon, which you can see in the Museum of Modern Art in Manhattan. Glaser himself compared the iconic design to the declaration of love on a tree trunk. The final version of the logo is in American Typewriter typeface. Its clear, simple message that appeals to your feelings has resonated with so many people, it’s still used today.

#25

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#26

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#27

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Maybe the T-shirts on this list aren’t as iconic as the ones we talked about. However, they are eye-catching and will illicit reactions from people around you. And isn’t that what good styles do?