The 100 Most Iconic T-Shirts of All Time

Have a Nice Day

The road to iconic tee was a lot longer than Forrest’s run, starting in 1943 as a Swedish film promo and blossoming as the novelty brainchild of two guys from Philly as “Have a Happy Day” in 1972. Somehow “happy” later got switched to “nice.”

The Tie Dye Tee

Rit Dye, a core component in tie dye is being phased out. The manufacturer of the product launches a huge marketing blitz aimed at the free-spirited youth of the time, due to the psychedelic colors used in the dyeing process. It catches on with hippies around the U.S. and takes off.

Che Guevara

A Marxist figure turned commercial fashion statement, there’s a degree of irony in this entry.

RUN DMC

Considered to be one of the most influential hip-hop groups in history, Run-D.M.C. started out performing a new type of rap music in the early 80s. Their innovative musical style helped them achieve fame early, and were the first hip-hop group to be nominated for a Grammy and achieve gold-album status. This block letter tee showing off their emblem is bold, memorable, and represents hip-hop in its original form.

Pink Floyd – Dark Side of the Moon

Wear this entry, play the Wizard of Oz, and just… Woah, man. An iconic image for one of rock’s most emblematic albums, Pink Floyd inspires generations of listeners to try looking to the dark side.

Tuxedo T-Shirt

The perfect mix of high and low, the tuxedo t-shirt is a timeless addition to any wardrobe. Pair with a fine wool slack for that special occasion, or jeans and chucks for the 80s alternative prom look.

Hard Rock Cafe

If you’ve done any traveling, you’ve probably seen someone wearing a Hard Rock Cafe T-Shirt at some point. Each Hard Rock Cafe, along with its vast array of music memorabilia typically sells a shirt with its city name in their gift shop. With over 100 restaurants having opened up all over the world, these shirts have become something of a collectible over the years.

Batman

Na na na na na na na na na na na na na na na na na na na na na na na na, BATMAN!

Superman

The literal power of this phenomenon can be seen on t-shirts everywhere and with the seemingly endless television & movie remakes in nearly every decade of Superman’s existence, this story (and t-shirt design) isn’t getting old any time soon.

Rolling Stones “Lick”

Alternative album cover for one of the best rock albums of all time, The Rolling Stones’ “Lick” graphic from the Sticky Fingers LP quickly becomes one of rock ‘n’ roll’s most recognizable symbols.

COLLEGE

Providing comic relief in the film Animal House, John Belushi has become something of an icon for college guys everywhere based on his portrayal of oafy fraternity bro, Bluto. A poster of him wearing this shirt (really a sweater) can now be seen on dorm room walls across the country.

Vote for Pedro

Wildly popular after the cult hit movie Napoleon Dynamite was released in 2004, the Vote for Pedro shirt has since gained mass appeal. While it’s a relatively simple design on a white/black ringer tee, the movie created quite a visual imprint during Napoleon’s famous dance scene.

I ♥ NY

In an almost eureka moment, designer Milton Glaser sketches “I ♥ NY” on a napkin and the logo appears on T-shirts soon after. It then becomes one of the most worn t-shirts of all time. And our most iconic!