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50 Coolest T Shirts Of All Time!

by Henna Ray Tweet - in Tshirt Design

Cool T-shirts

Last updated on February 27th, 2023

There has been a long list of fashion trends that have come and gone in 2018. But the one trend that has managed to retain its position is t shirts. T-shirts are one of the most comfortable and coolest pieces of a wardrobe staple. This no more casual attire has become much more than it was earlier. Today, companies are creating the coolest t shirt designs for their business promotion.

T shirts are only a single piece of clothing that can be worn with different styles of bottoms like skirts, jeans, shorts, stockings, chinos, etc. This has made it a popular staple among people of all ages.

Every person wants to make an impression that lasts. Well, there are a lot of ways to do that, but the first thing that any passer-by noticed is the way the other person is dressed up. If you want to stand out in the crowd, you need a unique t shirt. The great thing about custom t-shirts is that one can flaunt their personality by printing cool graphics or sayings.

The trend of creating custom t shirts has grown enormously. This has made many people start their entrepreneurial journey with t shirt making business.

Whether you want to create a t-shirt for yourself or for business purpose, we have come up with coolest t-shirt designs of all time that can help you to set apart from others.

Check Out The 50 Coolest T Shirt Designs Of All Time

01. Hard Rock Cafe

Hard Rock T-Shirt Design

If you have travel, you probably have seen people wearing this cool t shirt. The t shirt has been around for years and with more than 100 restaurants globally, this has become a collector’s item. The best thing about the t shirt is that it has a name of the city under its famous logo.

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02. Superman

Superman T-Shirt

Everyone knows about this classic and motivational fictional character of DC comic. The symbol used on the suit of Superman has become the most popular icon in the world of fashion. From kids to teens, adults to old, everyone loves to wear this cool t shirt as it makes them feel like it gives power to their inner strength.

If you look around, you will get to see different varieties in Superman tshirts. If you want to create your own style by using this iconic logo design, you can do this by using t-shirt maker tool.

03. Tuxedo T-Shirt

Tuxedo cool T-shirt

This timeless wardrobe addition has an image of white tuxedo shirt, lapels of a jacket, and a bow tie. This cool t shirt can be worn at the beach or parties. You can also gift this t-shirt to your dear ones. Just like a regular tuxedo, one can get a shirt design in different colors.

04. I ‘Heart’ NY

NY T-Shirt Design Online

If you have ever been to New York, you probably have seen a large population wearing this cool t shirt. The great thing about this tee is that it was originally designed to promote tourism in 1977. The t shirt design became popular when many visitors and locals wore this to support those who got affected by the September 11 terrorist attack. The t-shirt has become one of the most worn tees of all time.

05. Don’t Mess With Texas

Texas T-shirt

The slogan ‘Don’t Mess with Texas’ was commissioned by the Transportation Department of Texas to reduce the wastage on the roadways of Texas. The slogan became so popular that it got picked by apparel brands. Many apparel companies started printing tshirts with this slogan.

T-shirt design

06. Bart Simpson

Simpson t-shirt

The Simpson, one of the longest running animated TV series in American history, is still ruling the heart of the audience. The TV series inspired many t-shirt makers to create coollest t shirts by using the famous character ‘Bart Simpson.’

07. The Rolling Stones

Rolling Stone T-shirt

Inspired by Mick Jagger’s pout and tongue, John Pasche (the designer) created the ‘Lips’ logo for the famous English Rock band in 1971. The logo soon became the iconic symbol for the rock ‘n’ roll scene during the 60’s. It didn’t take long for this design to be printed on t-shirts all over the world.

08. Charlie Brown

Charlie Brown T-Shirt

Charlie Brown, one of a widely known cartoon character, may not have had good luck in life, but he had created the famous look for himself. Charlie always used to wear black shorts and a polo t-shirt with black zig-zag stripes. His zig-zag striped tee became so popular that it soon becomes famous among the audience.

If you have your own t shirt design ideas and want to create a cool t shirt on your own, then show your creativity by using this t-shirt maker tool.

09. Pink Floyd – Dark Side Of The Moon

Pink Floyd T-shirt

This t shirt design was inspired by the ‘Dark side of the Moon’ album of Pink Floyd. The album got released in 1973, and since ever then the popularity of this design has not decreased. The t-shirt has always a go-to for many rock fans.

10. D.A.R.E

D.A.R.E. T-Shirt Design

In 1983, in order to prevent teenagers to use drugs and violence, the International Drug Abuse Resistance Education Association ran a program. During the program, this unique t shirt was provided free of cost to all the people who support the program.

It came to a famous piece of clothing back then. Today, with a global presence in more than 52 countries, D.A.R.E t-shirts continue to retain its position in the fashion industry.

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11. I’m With Stupid

I'm with Stupid

This funny t shirt has been popular among people for many years. It is the founder of directional tshirts that cause snigger at the cost of an innocent bystander. The tshirt has been made into different variations. If you want to customize it according to your style, you can ask a shirt maker to do it for you.

12. Keep Calm And Carry On

Keep Calm And Carry On

Originally this t shirt was designed during the Word War-II to raise the morale of British people, but soon it became a mantra around the world. Today, you can see the endless possibilities with this rhyming motto.

13. Bob Marley

Bob Marley

An international musical and cultural icon, Bob Marley’s image is one of the most popular pictures of all time. It has been estimated that 25 million t-shirts designed by using his image have been sold worldwide.

It has made this t-shirt as one of the highest selling graphic tees in the market. His picture is so immortal that you can see it on posters, custom sweatshirts, and many other places.

14. Just Do It – Nike

Just Do It - Nike

One of the world’s largest and most popular brands uses his trademark ‘Just Do It’ on t-shirts to bring a sports vibe with everyday wear. You will find this iconic and coolest t shirt in ever t-shirt lover’s wardrobe.

15. Mickey Mouse

Mickey Mouse

With the growing popularity of Disney charter ‘Mickey Mouse’ Sam Kantor founded a t shirt printing company with the solo licence to produce Mickey Mouse t-shirts. It is probably the one piece of clothing that people wants to wear during their trip to Disney World. This cool t shirt brings a smile on everyone face.

16. Peace Sign

Peace Sign

The peace sign was originally designed by Gerald Holtom (British artist) in 1958 for The Campaign for Nuclear Disarmament (CND). T-shirt makers started using this internally recognized symbol to give people a chance to express their thoughts through t shirts.

17. Harley Davidson

Harley Davidson

Who doesn’t love Harley Davison’s bike? If you are also a big fan, then this cool t shirt should be there in your wardrobe. You can customize it by using your own picture sitting on the bike with the company logo. Take the help of professional graphic designer or use the t-shirt maker tool to design it according to your style.

18. Vote For Pedro

Vote For Pedro

Soon after the release of the classic movie Napoleon Dynamite, this cool shirt design gained a lot of popularity. In the movie, the character ‘Pedro’ distributes t-shirts for his campaign with the quote ‘Vote for Pedro’ printed on it. Though the shirt design is simple, it had a great impact on the audience and soon become the iconic and coolest t shirt of all time.

19. Frankie Say Relax

Frankie Say Relax

In 1984, to revoke the censorship of the song ‘Relax’, the journalist and co-founder of ZZT (Frankie’s record label) printed the slogan ‘Frankie Say Relax’ on t-shirts. The block letter tee design became such a big hit that even today, it acts as a graphical inspiration to many of the designers.

20. Ghostbusters


This logo design from the iconic movie ‘Ghostbusters’ is recognized all around the world. You can show your love for the classic movie with this unique t shirt. Or you can gift it to a Ghostbusters lover. The choice is yours!

21. …All I Got Was This Lousy T-shirt

...All I Got Was This Lousy T-shirt

This humorous t-shirt comes in various forms and is often kept as a well-spent holiday memento. By taking the graphic design services, you can get your own version of a t-shirt.

22. I Want My MTV

I Want My MTV

MTV graphic tees have been in fashion since the time when the channel was all about music. If you have spent the 90’s watching MTV, then this cool t shirt should be there in your wardrobe. You can customize your t-shirt with its updated new logo design. How? Try the t-shirt maker tool on Designhill. The easy-to-use tool has a lot of in-built graphics, icons, colors, etc. to choose. You can even upload your own design.

23. Coca-Cola


Coco-Cola has made a name from themselves not only through their beverages but also through their cool t shirts. The plain t-shirt with the iconic logo design has been there for years and won the hearts of millions of consumers globally. The trend of this t-shirt seems to continue in the coming years as well.

24. Lifeguard


Inspired by the American TV show ‘Baywatch’, this red t-shirt with a white cross can be seen being worn on beaches or pool facilities. A person wearing this t-shirt is capable of saving your life – well, there is no such guarantee, but it’s a coolest t shirt anyway!

25. Jack Daniels

Jack Daniels

T-shirt with the popular alcohol label perfectly goes well for Friday night party. A white print on the black tee makes this t-shirt looks really catchy.

26. The Godfather

The Godfather

One of the best and Oscar-winning award movies gave birth to this unique t shirt. The iconic logo on a black t-shirt makes it look a cool wearable. So next time, whenever you plan to watch this movie with your dear ones, show your love for the movie by donning this t-shirt.

27. Abbey Road

Abbey Road

This cool tshirt design includes John Lennon, Paul McCartney, Ringo Starr, and George Harrison crossing the Abbey road. The inspiration for this shirt design has been taken from the cover of their album.

28. The Flash

The Flash

From kids to teens, adults to old, superheroes have always ruled the heart of the audience. What could be cooler than wearing a signature lightning bolt logo printing on a t-shirt or a custom kids t shirt? If Sheldon is your favorite character, and if you want to appear like him, there’s no better attire than a Flash t-shirt.

29. Rock The Vote

Rock The Vote

Rock the Vote is a political movement that got started in 1992 to build the political power of young people. It has totally revolutionized the way we use technology, culture, art, music, etc. The popularity and success of the campaign gave birth to this coolest t shirt of all time!

30. Captain America

Captain America

Captain America – the most famous and beloved fictional superhero of Marvel Comics. The popularity has urged the brand to come up with a wide range of coolest t shirts. The t-shirts have the logo and the picture of Captain America. Get your favorite Captain America t-shirt and grab the attention.

31. Nirvana Smiley Logo

Nirvana Smiley Logo

There are several different theories on the origin and meaning of this iconic Nirvan Smiley face logo design. No matter whoever designed this logo, the symbol has gained a lot of popularity and is widely used on t-shirts, bumper stickers, posters, etc.

32. Jurassic Park

Jurassic Park

When you think about dinosaurs, which is the first movie that comes to your mind? We bet, you say Jurassic Park. It is a masterwork of shooting with men dressed as Velociraptors and robotic dinosaurs. Bringing that masterpiece on t-shirts turned out to be a great decisison.

33. FCUK (French Connection)

FCUK (French Connection)

A UK-based international wholesaler and retailer in fashion and homeware started ruling the market when the brand started using ‘fcuk’ in advertising. The slogan became so popular that it never goes out of style. Adding ‘UK’ after ‘FC’ helped the brand in getting more fan following. Even after 30 years, the t shirt design is considered to be one of the coolest t shirts of the time.

34. Where’s The Beef?

Where’s The Beef?

This phrase first came into public attention as a slogan for the fast-food chain Wendy’s. The strategy behind the campaign was to differentiate competitors hamburgers from Wendy’s bun. The slogan became so popular that it started printed on t shirts and bumper stickers. Today, you can see the endless possibilities with this phrase.

35. Jesus Is My Homeboy

Jesus Is My Homeboy

There is a very interesting story behind this slogan. During 80’s a man named Van Zan Frater was assaulted by a gang. When one of the boys pointed a gun on Frater’s head, other gang members shouted ‘Kill him, Homeboy.’ Frater prayed to God to save him and replied to attackers ‘Jesus is my homeboy, and he is your homeboy too.’ After hearing this, the attackers let him go.

After this incident, Frater designed this slogan on t-shirts. The t-shirt became popular in the mid-2000s when celebrities like Ashton Kutcher, Brad Pit spotted wearing it. Show others who has your back by wearing this coolest t shirt of all time!

36. We Can Do It

We Can Do It

The poster ‘We Can Do It’ was first introduced during the American World War-II to boost the morale of female workers. The image was again rediscovered in the 80’s and used to promot9oe feminism and other political issues. Today, the image is widely known and has adorned t-shirts, coffee cups, tattoos, and many other products.

37. Camouflage


This military pattern t-shirt is a great way to inject energy to your wardrobe. Whether you want to wear it in a casual evening or set an airport look, this Camouflage print can give a right attitude and uber cool style statement.

If you are planning to have a customized t-shirt with this print, we would suggest you to avoid putting any logo design on the t-shirt. Pair this print with straight fit jeans (not blue) and smart sneakers to get a cool look.

38. Austin 3:16

Austin 3:16

When WWE/WWF wrestler Steve Austin beats Jake ‘The Snake’ Roberts in 1996 historic match, the most iconic and popular phrase Austin 3:16 came into existence. The phrase started to appear in the WWF events and on t-shirts. Soon it became one of the hottest and coolest t shirts in its history. Even today, you may come across with a fan wearing a t-shirt with this phrase.

39. YOLO


The phrase ‘You Only Live Once’ was first created by the rapper Drake. American Dialect Society nominated this phrase as 2012 Word of the Year. You will get to see this highly popularized phrase everywhere such as custom hats, t-shirts, bumpers, social media, etc.

40. Anarchy Symbol

Anarchy Symbol

Anarchists have used certain symbols for their cause, which includes the most significant circle-A and the black flag. Though the American’s punk rock phase has passed, t-shirts with this symbol are still giving a rebellious reminder. You can customize the t-shirt by uing t-shirt maker tool.

41. Woodstock Festival

Woodstock was a music festival held on a dairy farm in the northwest of New York City. The event attracted a large number of audience and was also captured in the Award-winning documentary movie ‘Woodstock.’

Woodstock Festival

Although the originals of this classic are very rare, the t-shirt is still a hot favorite among Americans. If you want to create your own coolest t shirt with the same design, then use our t-shirt maker tool and order for printing.

42. Union Jack

Union Jack or Union Flag is the national flag of the United Kingdom.

Union Jack

The well-known stripes became popular when Def Leppard’s Joe Eliot wore the sleeveless t-shirt in a concert.

43. Property Of…

During the period of 30’s and 40’s, football players at the University of Southern California started donning similar t-shirts under their shoulder pads to prevent chafing.

Property Of...

The shirts became so popular that other students started wearing them casually. In response, the university stenciled ‘Property of USC’ on its t-shirts to prevent crime. Today, you can see the endless possibilities with one of this coolest t shirt design.

44. Lennon’s New York City

Just before the photo shoot, John Lennon bought this t-shirt from a street vendor for $5. The photographer, Bob Gruen, asked him to put on a t-shirt for the shoot and show what being a New Yorker meant to him.

Lennon’s New York City

The sleeves of the t-shirt were cut-off with a knife for a tougher look. The impact of his images with the t-shirt was such that soon it became one of the most iconic and coolest t shirt.

45. Three Wolves Howling At The Moon

Who hasn’t seen this shirt? A classic black t-shirt with the three wolves howling at the moon gained popularity when an anonymous customer left a hilarious 5-star review on Amazon.

Three Wolves Howling At The Moon

This cool t shirt was designed by Bulgarian artist Antonia Neschev and produced by the U.S based company ‘The Mountain.’

46. Kiss Me I’M Irish

‘Kiss Me I’M Irish’ phrase is connected with St. Patrick’s Day. It comes from the legend of Blarney stone, which is believed to bring luck and power of expressiveness to those who kiss it.

Kiss Me I’M Irish

This cool t shirt has been a classic go-to during March. If you want to create your own version by using this phrase, then you can do it either by taking the help of a professional graphic designer or by using online t-shirt maker tool.

47. The Tie Dye Tee

The word ‘tie-dye’ first come into view during the 60’s in the U.S. Hippies, who protested the Vietnam War and promoted love and peace, started wearing clothes with psychedelic designs and energetic colors.

The Tie Dye Tee

The t-shirts soon became popular among America’s youth. Today, you will get to see this t-shirt in music scenes, school projects, birthday parties, and many more places. To get your style of tie-dye, get the graphic design services from the World’s most popular freelance graphic design platform.

48. James Dean’s Plain White T-Shirt

The magic of this cool white plain tee is still unmatched. The t-shirt gained its popularity when James Dean showed up with a white plain t-shirt and leather jacket in the classic 1955 movie ‘Rebel Without a Cause.’

James Dean’s Plain White T-Shirt

People started following his style and the white plain tee turned into a classic staple.

49. Run DMC

Run-DMC was widely acknowledged American hip-hop group. The group was not only famous for their music but also for the fashion statement that they had struck.


This t shirt design is a great way to show appreciation and love for the rap pioneers.

50. Che Guevara

Our list of coolest t shirts is incomplete without mentioning the Che Guevara trend. The t-shirt features an image of Argentinian-born revolutionary Ernesto “Che” Guevara.

Che Guevara

The image is a well-liked design for clothing and is popular among younger adults.

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There is definitely something special in cool t shirts. The moment you wear them, you start feeling cool from inside. You start getting the attention, the courage to stand against the wrong. Cool t shirts give a boost to start the journey in a new direction. Which one is your favorite coolest t shirt from the above list? Don’t forget to share it in the comment section below.

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Hi! I am professional Logo designer and an aspiring blogger. An expert on various tools Like Adobe Photoshop, Illustrator and Coral Draw, I have successfully designed several application interfaces, android apps, logo designs, business card designs, letterhead designs, envelop designs, flyer designs, brochure designs and web banners. Twitter



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