90s T-Shirts You Regret Wearing as a Kid in the '90s  

Jacob Shelton
10.2k votes 1.1k voters 69.3k views 20 items

List Rules Vote up the sick tees you totally rocked in the '90s, but are feeling some serious regret about today.

The 1990s were a peak time in history for terrible fashion, and among that bad fashion were some truly regrettable '90s t-shirts. For some reason we all thought it would be a great idea to wear giant shirts covered in cartoon characters who were dressed like Tupac, and even bigger shirts that were simply advertisements for two wheeled death machines. If you were alive during the last decade of the 20th century, you wore some of these embarrassing '90s t-shirts and there’s no reason to try to hide it.

No one was cool in the '90s. You maybe thought you were cool in your Tommy Hilfiger shirt with the extra wide pseudo American flag, but you were a dork and it’s time to admit it. It’s hard to distinguish between bad shirts from the '90s and the worst '90s t-shirts so we need your help. Vote up the now-embarrassing shirts you totally rocked in the ‘90s and if you’re still wearing your B.U.M. Equipment tee to the beach, leave a comment so we can file a report with the fashion police.

1 520 VOTES

Marlboro

Marlboro is listed (or ranked) 1 on the list T-Shirts You Regret Wearing as a Kid in the '90s
Photo: lanikosam/Tumblr

Why were our parents letting us wear shirts that advertised cigarettes? Is it because they spent thousand of dollars to save up points and didn't want the cash to go to waste, or were they a part of the Marlboro department? These shirts were always XL (we'll give you a million dollars if you can find a medium) and they screamed to everyone nearby that your house smelled weird.

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Is this embarrassing in hindsight?
2 517 VOTES

Unironic Wolf Shirts

Unironic Wolf Shirts is listed (or ranked) 2 on the list T-Shirts You Regret Wearing as a Kid in the '90s
Photo: Imgur

Weren't we all so smart and funny in the early 2000s when we started wearing three wolf moon shirts? What about our decision to wear them in the '90s? Were we accidentally flexing our ironic detachment muscles a decade early or did we just think wolves were cool? Either way it was a bad choice.

329 188
Is this embarrassing in hindsight?
3 511 VOTES

Space Jam is listed (or ranked) 3 on the list T-Shirts You Regret Wearing as a Kid in the '90s
Photo: thegolddig/Tumblr

If you were alive in the mid-'90s you were either wearing a lot of Space Jam merch or you were wishing you could wear a lot of Space Jam merch - which is ridiculous by the way. There should have been one Space Jam shirt, and it should have featured Bill Murray hitting a hole in one.

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Is this embarrassing in hindsight?
see more on Space Jam
4 510 VOTES

Orca Shirts

Orca Shirts is listed (or ranked) 4 on the list T-Shirts You Regret Wearing as a Kid in the '90s
Photo: Imgur

When did we collectively agree that orcas were cool? Did we wear these shirts because of Free Willy? Or is there simply something hypnotic about the orca's black and white markings?

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Is this embarrassing in hindsight?