The Most Iconic T-Shirts of the 80’s-90’s

And Iconic Crooked Monkey Original Tee's

The 80’s and the 90’s are decades that hold memories, music, and icons that will last for centuries to come. Being that we at Crooked Monkey are really into t-shirts and other forms of apparel, we thought it would be fun to honor the 80’s and 90’s for the pure genius they produced but are often not recognized for, their t-shirts!

Check out our list of the most iconic 80’s-90’s t-shirts and then take a look at how we at Crooked Monkey have built upon that age old gold to develop some of this centuries hippest t-shirts!

1. HyperColor

Picture this: It’s 1991 Full House is on your television, Beauty and The Beast just hit the big screen, and HyperColor t-shirts are everywhere!

Otherwise known as the “mood-ring” of the 90’s, these body heat initiated color changing t-shirts were all the rage earning them a spot on our list of iconic 90’s t-shirts.

In fact, between February and May 1991, the company sold a total of $50 million worth of color-changing apparel.

Unfortunately, the trend didn’t make it to see the new millennium, but we’re still intrigued with this mysteriously rad fad!

2. Tie-Dye

Thanks to a couple of hippies, a box of Rit Dye, and a psychedelic vision- the tie-Dye t-shirt trend first came to life in the 1960’s, but out lived many other trends of the generation.

In the 1980’s, new types of dye hit the market that had more color and shade variety as well as staying power.

From there, the opportunity for tie-dye was endless and the trend took off- landing them a spot on our list of iconic tee’s!

3. Run DMC

Run-DMC was an American hip hop group from Hollis, Queens who is now considered to be one of the most iconic groups of the 80’s.

Although the logo designed by Stephanie Nash in 1986 was only ever featured on the groups singles or compilations, it hit t-shirts and other forms of apparel all over the world.

Now known as one of the most iconic logos of all time, it’s no surprise that Run DMC also found its way on to this list!

4. D.A.R.E

The D.A.R.E t-shirt was first designed as a piece of merchandise for a drug awareness program that was initiated in Los Angeles in 1983.

Although the program proved itself to be relatively unsuccessful, the anti-drug t-shirt became a stoner favorite.

After becoming a staple tee for actors, fashion designers, and all house party goers of the 90’s- the shirt became globally recognized therefore easily earning its number four spot on our list of iconic 80’s-90’s t-shirts.

5. T-Shirt Tuxedo

Although we all love a man in a tuxedo, not every man loves sporting one.

Luckily, someone in the 80’s had the bright idea of printing one on a t-shirt. It’s casual by nature of the tee, but it’s bow tie, tuxedo shirt, and lapels screen-printed on the front most definitely spruce up the presentation and have the potential to lighten up the mood of any stuffy old formal event.

Although the personality of those who sport this tee often reflects that of someone who couldn’t care less what the rest of the world thinks… We mean it in the nicest way possible and strongly support the return of this 80’s gem!

6. Peace Frogs

Peace Frogs is an American company that was founded in 1985.

The company first began by producing a line of multi colored shorts with international flags, and because the frog is the American Indian symbol for peace, the name Peace Frogs was chosen.

As the popularity of the frog continued to increase well into the 90’s, the focus shifted from the flag to the amphibian, and peace Frog shirts took off everywhere- earning them the title of a 90’s t-shirt icon

7. Nirvana

The iconic Nirvana logo made its original debut on a poster that was promoting the bands release party for its breakthrough album in 1989, and has since been printed on an endless array of the bands merchandise and sold worldwide.

Although the logo endures global recognition, the inspiration for the design is still a mystery and many believe the bands late lead singer Kurt Cobain to be the only person to have known its true meaning.

The simplicity mixed with the riddle of its origin is believed to be what has driven this logos popularity around the world and right on to our list of iconic 80’s and 90’s t-shirts.

8. Austin 3:16

Austin 3:16 is a catch phrase that was born from WWE wrestler Stone Cold Steve Austin at the WWE King of The Ring pay per view match in June of 1996.

At this noteworthy encounter, Stone Cold Steve defeated his opponent Jake “The Snake” Roberts who at the time portrayed a former alcoholic who defeated alcoholism through his faith and regular reference of the bible verse John 3:16.

After Austin was victorious over his opponent, he mocked him stating “Austin 3:16 says I just whipped you a$.”

The catchphrase was then trademarked, and landed itself on t-shirts all over the country, and has now touched itself down on Crooked Monkey’s list of iconic tees from the 80’s and 90’s.

9. Property of Shirts

The University of Southern California started a trend for the ages after adding “Property of USC” to their football teams workout t-shirts.

Upon their reveal, the rest of the student body liked them so much that they began stealing them. To prevent further campus theft, the school began adding the saying to a variety of student apparel and the trend then took off nationwide.

As the 80’s rolled around, fans everywhere were proudly supporting their teams in their “property of” tee’s, making them look as iconic as they come!

10. Don't Worry Be Happy

In September of 1988 Bobby Mcferrin released his single “Don’t Worry Be Happy.”

The song then became an unofficial Jamaican anthem after hurricane Gilbert hit the island that very same month.

Because of its Jamaican association, the song and the phrase are often attributed to Bob Marley who actually passed away seven years before the songs release.

Maybe the correlation between the two inspired the shirts popularity, or maybe the phrase was just destined to be world renowned!

Regardless, the Don’t Worry Be Happy tee’s find themselves a well deserved spot on our list of 80’s and 90’s iconic t-shirts!

11. Teenage Mutant Ninja Turtles

If you were a kid during the 80’s or 90’s, then you definitely spent some time reading, watching, or playing with the four kick butt amphibians we came to know and love as the Teenage Mutant Ninja Turtles.

When the comic’s writers first came up with the idea in 1983, it started as a complete joke. Little did they know, their drawing would grow to become one of the most recognized comic franchises of all time.

With success like that, it’s no surprise they ended up with t-shirts and no less shocking that those tees found their way on to our list of 80’s icons!

12. Hulkamania

After being offered a role in the movie Rocky 3 in 1982, Hulk Hogan was told by Vince McMahon that if he took the job, he was fired from his job with WWE.

Hulk decided to defy his suggestions, taking the job and moving to Japan to continue as a wrestler.

Unfortunately, he wasn’t making enough money overseas and turned to selling t-shirts out of his car for extra cash.

He produced a couple of duds before hitting the gold with Hulkamania, and it wasn’t long before the shirts were seen everywhere throughout the late 80’s and 90’s earning them the title of iconic!

13. John Deere

John Deere holds one of the world’s most recognized corporate logos.

The company strategically made the colors yellow and green their own as they grew to become the gold star standard for farming equipment.

In the mid 90’s the country boy look took off, and John Deere Apparel was all the rage.

Paring the iconic logo with a t-shirt or hat was an instant success, and the farmers trend was born!

14. MTV

On August 1st, 1991 the world was introduced to Music Television for the very first time.

After a dramatic countdown, the music video for “Video Killed the Radio Star” hit the airwaves and thousands of people all over the country fell in love with MTV.

Not long after the premier, the “I want my MTV” t-shirt was born.

Over the years, the channel has evolved from music videos to reality series, but the shirt has remained a symbol- locking it down on our list as one of the most iconic tees of the 80’s and 90’s generation!