Top 50 T-Shirts of all time: 30-21

In this post, I’m going to get my top T-Shirts of all time down to the final 20. In the last post, we saw some great entries which could have easily got into the top 20 but I think that the T-Shirts below all have something else which helped to set them apart.

Read on below to see the list from 30-21 and, as always, let me know in the comments if you agree or disagree.



The Cookie Monster was created way back in 1966 and since then the T-Shirt sales continue to come in.

The Cookie Monster found his fame on children’s favourite Sesame Street and he instantly became a fan favourite thanks to his love of cookies. Now, he’s still popular with those who grew up through that era, and much like other children’s TV program merchandise, the T-Shirt sales have continued thanks, in part, to nostalgia.



Harley Davidson was once synonymous with the “Hell’s Angels” but it quickly became a favourite design for everything who enjoyed motorbikes and the open road.

The Harley Davidson T-Shirt is the perfect example of what happens when a brand becomes more than just a type of product as you can walk into specialised shops which sell Harley Davidson bags, mugs, T-Shirts, baby clothes and much more.

What’s more, the T-Shirt and other merchandise sales have made the Harley Davidson logo one of the most easily recognisable throughout the world.

28. The Camouflage T-Shirt:


The Camo look is one of those looks which just never seems to go out of style. Whether it’s being worn by people in the military, by those hunting or paintballing or whether it’s part of a new look that you’re going for.

Camouflage T-Shirts, jackets, and trousers are just one of those styles which you can wear year after year without needing to update your wardrobe.

While I don’t wear camouflage anymore, I have done in the past and I’ve owned many an item of camouflage clothing which is the reason why it makes it into my top 30.



If you got the quote from the title then I can pretty much safely bet that you’ve either got or previously owned a Captain America T-Shirt.

This simple design takes the Captain’s iconic shield and puts it onto a T-Shirt. The simple design of the shield (a single white start on a bulls-eye surrounded by red and white rings of America) has become one of the most famous icons around the world.

Thanks to the new movies, it’s become the perfect way for young minds to show off their patriotism.



The “I’m With Stupid” T-Shirts were probably the start of the funny T-Shirt culture that we’re experiencing now. The T-Shirt was famous for it’s simple, subtle humour and allowed the wearer to discreetly mock their friends who are standing to their side.

While the T-Shirts weren’t exactly well designed they were incredibly popular and they’re still worn today throughout the world.

Not only that but a T-Shirt which can inspire a whole culture of humorous, mocking T-Shirts fully deserves its place in the top 30 T-Shirts of all time.



Whether you’ve read Mario Puzo’s book, or if you’ve been fascinated by the oscar winning film by Ford Coppola – The Godfather has opened up a whole new fascination with the Mafia both in the UK and in America.

Since the movie release, the film has rightly been recognised as one of the greatest films of all time and the actors, Al Pacino and Robert Di Niro, have also gone on to become some of the biggest stars to ever appear on screen.

To this day, The Godfather remains one of the greatest films ever made and merchandise for the movie still sells throughout the world.



In 2004, cult hit movie Napoleon Dynamite was released and since then the wildly popular “Vote For Pedro” T-Shirts gained instant popularity.

The simple design of red text on a white T-Shirt gained mass appeal thanks to the brilliant film which remains one of my all-time favourite films.

What’s more, “Vote For…” T-Shirts have become popular in the custom T-Shirt world with people getting their own names printed to create some cool custom clobber which references a brilliant film – Oh, and who can forget that epic dance scene?



Baywatch helped to make lifeguards jobs more glamorous and gave us stars such as Pamela Anderson and David Hasselhoff.

It also created merchandise such as Baywatch T-Shirts that are still popular today. The T-Shirts continue to sell well and it remains a popular choice when it for stag parties when they’re travelling abroad.

Whether it’s a T-Shirt or a vest, the bright and in your face designs are seen throughout the world on popular beaches and stag resorts around the world.



Disney merchandise has always sold well and it will continue to do so – more so since the purchase of Star Wars.

One of the original characters, Mickey Mouse, helped to raise the popularity of Disney merchandise since Tropix Togs, a Miami-based T-Shirt company, bought the exclusive rights to print the figure onto a T-Shirt.

Since then, Hollywood stars, such as Emilio Estevez, have been spotted wearing the T-Shirts which has helped to make them cool for adults as well as children.



The Beatles were probably the most popular band to ever come out of the UK. Their music is still listened to around the world and their fan base continues to grow even after the band stopped releasing music.

Their merchandise comes in many different forms, including the famous Abbey Road image above, and each piece of merchandise sells exceptionally well.

The Abbey Road crossing image has since become one of the most famous and recreated images of all time and continues to be a massive seller to this day.

So this completes my list of T-Shirts from 30 down to 21. Next week I will look at the top 20 and finally get down to the top 10.

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