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10 Most Iconic Shirts in the History of the Tee

Updated: Apr 25, 2022

Firstly, can we just stop to admire the beauty of this man?

...Good GRIEF could James Dean wear a white tshirt well.

And speaking of white tshirts, I am SUPER excited for today's post.

Tees became popular in the 19th century, when laborers began cutting their jumpsuits up for a cooler (as in temperature) style.

FINALLY getting the hint, manufacturers started jumping in on the brilliance of the trend...and the tshirt as a style was born.

Around 1920, the term "t-shirt" was created and it started making its way more into the fashion scene. By the mid 1920's, the tee was no longer just for sweaty, greasy mechanics and Navy officers.

It was now for the greasers and the cool kids.

With all of the history the tshirt has...what have been some of the most iconic tees to come to the market? I wanted to dive into this question, so below are my 10 top tees of the last 100 years.

10 Best Selling TShirt From the Last 100 Years

These aren't necessarily in any particular order...but the obsession for these designs has yet to die down. (We don't sell all of these shirts, since we DO conform to trademark laws...but I'll link to any of them that we do sell!)

1. The White Tee

Dean, Brando, Beiber, Styles...these fellas all have one thing in common (aside from their hot factor). These style icons have all leaned into the white tshirt MORE than once to make a fashion statement. In "Rebel Without A Cause" James Dean brought the white shirt to the forefront of popular fashion with his cool kid leather jacket, emo attitude, and sunshades worn at ALL times of the day/night. And the white tee trend just picked up speed from there. As you're watching your movies or reading your attention to how many times you see your favorite stars sporting this simple, iconic tee today.

2. Napoleon Dynamite's "Vote For Pedro"

In 2004, Jon Heder danced his way into people's hearts (and onto people's nerves) with his endearing role of Napoleon...a slightly weird and oddly self centered character growing up in a small town in Preston, Idaho.

He launches a campaign to help his friend Pedro win his election for class President, and thus is born the world's obsession with the "Vote For Pedro" tshirt that appears in the movie.

This is one of my favorite movies of all you bet your Summer Wheatley I have one of these comfy tees!

3. Charlie Brown this one MIGHT be a tee that a cartoon character wears, but it's spurred one of the most popular tshirt designs in the last 60 years! Charlie Brown, with his adorable football head and yellow and black striped tee, moped his way into our lives in 1948...and he's never changed his tee.

Whether you want to be Charlie Brown for Halloween or you just want to rep your love this iconic comic, this shirt will always be instantly recognizable.

4. The 1960's Smiley Face Tee

In 1963, Harvey Ball was hired by State Mutual Life Insurance company to design a button that would improve the moral of their employees. He was paid a whopping $45...and ten minutes later, this "button" would become a movement around the globe.

This smiley face has been used on tees, posters, buttons, bags, logos, and more! I don't know about you...but I use a smiley emoji at LEAST once a day when texting family and friends! (I might be a smiley face addict.

5. I Heart NY Shirt

This iconic shirt (and everything else under the sun this logo was put on) is probably one of my favorite histories from a popular design. In 1976, with NY tourism dropping off and residents fleeing to the suburbs for better living prices (and conditions), Milton Glaser was hired to start a campaign that would turn the city around.

Although the "I Heart" campaign was already thought up, Glaser's job was to come up with the iconic logo we know today. In the back of a taxi, he sketched out the logo in red crayon on a white napkin, and although it's been polished...the sentiment remains the same.

6. D.A.R.E.

The D.A.R.E. (Drug Abuse Resistance Education) program was created in 1983 (W00T!!! Word my birth year!) a push by the Los Angeles Police Department and the L.A. public schools to curb drug use and spread more awareness to the younger generations.

UNFORTUNATELY, it did exactly what it said it was going to do...and kids younger and younger began to learn about drugs, how to spot drug users and dealers, and the effects drugs can have. These facts were more education than deterrence...and the number of young drug users, dealers and deaths rose through the 80's and the 90's.

I, personally, remember being taught about drugs by the "D.A.R.E. Police Ice" rapper in the late 80's. He was a rapping cop, who came to preach the effects of drug use. The jury is still out on how effective this specific technique was.

6. Rolling Stones Licking Lips

The hot lips logo, or The Rolling Stones logo was originally designed by John Pasche in 1970. The Stones needed a poster for their 1970 European Tour. The band began to look for a design student to design not only the poster, but also a logo.

John Pasche was in his third year of college in 1970 when Mick Jagger approached him. Having accepted the commission, Pasche started working on the poster. For the logo, Jagger had suggested the tongue of the Hindu goddess Kali.

Pasche said at the time "The design concept for the tongue was to represent the band's anti-authoritarian attitude, Mick's mouth and the obvious sexual connotations. I designed it in such a way that it was easily reproduced and in a style I thought could stand the test of time.".

The logo has been re-created thousands of times with various versions, other than the bright red lips and tongue it was originally created with.

7. Nike's Just Do It

My dad had a shirt when I was growing up that said "Just Fixin' to Do It". It was the nineties and the Nike slogan was EVERYWHERE...even Texas, which is what the lazy slogan was based on.

In 1987 "Just Do It" was on TV, in magazines, on shoe boxes...and yes. On Tshirts. Even today, it's a mainstream slogan that still resonates with confidence in ANY well as resonates in the mainstream media.

We DID it, Shia....we did it.

8. The Tie Dye Tee

In the United States, tie-dye is MOSTLY associated with the 1960s counterculture — Woodstock, the Grateful Dead, flower power, psychedelia — and for those who came of age in the ensuing decades, with VERY messy childhood craft projects.

You can go earthy aesthetic...neon crazy psychedelic..and even tie dye with an image plopped on top!! Tie Dye came back in 2019 with a vengeance, and it's still going strong in 2022!

9. The Peace Sign

Much like the tie dye tee of the peace loving, psychadelic 60's...the peace sign tee has been a popular love promoting billboard for nearly four generations.

The modern peace sign was designed by Gerald Holtom for the British Camapign for Nuclear Disarmament in 1958. It became popular throughout the 1960's and 70's, during the Vietnam war, as a sign of peace and opposition to nuclear powers. And it's still used today to represent a longing for peace in a time of chaos.

10. Mighty Mouse

HERE HE COMES TO SAVE THE DAY!!!! Mighty Mouse is one of the oldest super hero characters, created as a parody of the JUST as mighty...Superman! Whether he's saving pearl or some other character in distress, he's always busy heroing it up in his tiny world.

Mighty zoomed into our hearts in 1914, and continues to be one the best selling characters on tee's, lunchboxes and other paraphernalia.

So, how'd I do??

There are millions of popular shirts out there...state shirts, college logo shirts, movie character shirts...the list just goes on.

But I really wanted to dive into some designs that truly HAVE shaped the way the fashion industry has fallen head over heals in love with the staple garment.

Want to check out more fun retro styles?? Shop by your favorite decade in the PuddinThreads store!

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