by Milind Yohann

Most Famous T-shirt Designs of All Time

From ‘I <3 NY’ to Frankie Say Chill, here’s a look at the most iconic t-shirt designs of all time. For the sake of keeping things generic, we will not be including artworks of Bands, Movies/Series or plain Brand logos/icons, unless they have a backstory that’s worth it.

1. 3 Howling Wolves 

We’re starting this list with a weird one. The 3 Howling Wolves T-shirt looks like your standard Direct-to-garment printed gothic looking illustration. A student decided to write a sarcastic review about it on Amazon, and that review went viral. 

How Viral? 

This Viral https://www.youtube.com/watch?v=meQ383gy5Rw

The original review is still up, if you can scroll through the thousands that have been added since. It’s now a trend to post a long sarcastic review on their page. Send us a screenshot if you posted one!

2. Vote for Pedro

Widely acknowledged as the most iconic t-shirt from the film industry - a simple roundneck t-shirt with the words Vote For Pedro on the front, This t-shirt design found itself under the face of cult classic hero Napoleon Dynamite. It was the highest selling piece of merchandise the franchise saw. Maybe it’s because it’s not just a t-shirt, it’s the spirit of Napoleon Dynamite’s search for skills, and whatever that last dance sequence was powered by.

3. Frankie Say Relax

Made Iconic for its appearance in the TV Sitcom Friends, the roots of this t-shirt have been twisted and retold as much as the lyrics to Hotel California. The fact is that it was official merchandise for a band called ‘Frankie Goes to Hollywood’. The more controversial theories are surrounding the band’s single titled ‘Relax’ and it’s suggestive nature (which got it banned by the BBC). More interestingly, it seems to be a targeted rip off of British Fashion Designer Katharine Hamnett’s political statement tees

Whatever the roots, the original is Frankie SAY Relax, not Frankie SAYS Relax

4. Plumtree- Scott Pilgrim 

Keeping aside the treasure trove of t-shirt designs that came out of this movie:

Let’s take a second to appreciate the brilliance of the Plumtree meta-tee.
Plumtree is a Canadian Indie rock band with some great music. Their most famous single, however, was the inspiration for Brian Lee O’Malley to create the legendary Scott Pilgrim. The single titled just ‘Scott Pilgrim’ drones the line ‘I’ve waited for a 1000 years’ which probably totes fan reactions to the movie that came out eventually. The band’s name and t-shirt appears in the movie at their first on-screen stage performance, check it out if you missed it before: 

5. ‘And all I got was this lousy t-shirt’ Origins

A trend that picked up rapidly in tourist spots and vacation destinations. We’ve all got one from that uncle that cracks bad jokes. But did you know that this dates back centuries? A 2000 year old Stylus was found in an excavation of London, with an inscription that, when translated essentially said ‘I went to rome and all I brought you was this pen’.

Read more here!

6. I <3 NEW YORK

We’ve seen it everywhere today, at Music Festivals, Malls, cities and towns across the world. Snap back to 1976, Milton Glaser is on his way to pitch an idea to save tourist in New York to the NY State Department of Economic Development. Milton makes history in the back of a taxi (some stories say at a bar), when he pulled out a scrap of paper and hastily scrawled the logo we know so well now.