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10 movies that prove the eternal coolness of Hawaiian shirts

Custom Hawaiian shirts will always be awesome, and don't you ever doubt that.

Some things operate outside the normal realms of fashion, and somehow manage to hold their own as the decades roll by. If there is an apocalypse around the corner, you can bet your bottom dollar that it won’t be enough to shake the likes of aviator shades, Levi jeans and canvas shoes off their perch.

You know what else fits into that category? Custom Hawaiian shirts.

Whether you’re chilling on the beach with an icy drink in-hand or simply looking to tell the world you’ve got it all worked out, you pretty much can’t go wrong. This unshakeable timelessness is reflected in Hollywood as well, even when you look at the sheer variety of movie characters that have donned the iconic thread.

If you are on the hunt for some custom-made Hawaiian shirts, check out our stuff here. All of our shirts are eco-friendly and sustainable, so you can feel nearly as good as you will look!

However, keep scrolling if all you want to do is remove any remaining doubt about how damn cool they are. Here are 10 eternally cool characters that have worn Hawaiian shirts in movies.


Now, we aren’t going to condone any of Tony Montana’s antics and neither should you. If we look beyond his occupation however and just take a second to appreciate his wardrobe, you might see things differently.

He remains one of the most iconic movie gangsters of all time, even nearly 40 years after the movie’s release. Without going as far as saying the delicious red Hawaiian shirt he wore for this scene is directly responsible, but to pass it off as a coincidence would be irresponsible.

Ace Ventura

Just to show it’s not all *bad guys who wear Hawaiian shirts, this classic Jim Carrey flick wouldn’t have been the same if he was wearing a polo. An essential part of what makes the movie so special, even Carrey himself would agree that the wardrobe guys absolutely knocked this one out of the park.

How Jim takes things to the next level though is that he mixes it up and wears several different ones throughout the movie. After all, having one how could one Hawaiian shirt possibly be enough?

*Sorry Tony, we know you don’t like being called a bad guy…

Runaway Bride

One of the best things about Hawaiian shirts (and there are plenty) is that they look good on anyone. Julia Roberts might be one of the most respected actresses of her generation and a global icon, but that doesn’t mean she’s too good for some tropical chic.

Her character might have had one or two commitment issues in the movie, but credit where it’s due for pulling off this look. Richard Gere looked phenomenal in his as well, it must be said.

22 Jump Street

This article isn’t titled “5 old movies where people wore Hawaiian shirts,” so it’s only right that we use some more recent examples as well. Jonah Hill absolutely rocks a gorgeous red number on the beach, and it’s a crying shame he doesn’t do it more often.

If you’re reading this Jonah, and I know you are, it’s time to get those floral designs out of the wardrobe.

Blue Hawaii

Whatever opinion you might have on Hawaiian shirts, there is only one Elvis Presley. Whatever The King touches turns to gold, so over 60 years later you wouldn’t need to change a thing about this look.

Stick on a Hawaiian shirt of your choice, pick up a ukulele and be who you want to be. If it was good enough for Elvis, you know you’ve made the right choice.

The Descendants

For going on 30 years now, George Clooney has been seen as the epitome of cool. He’s aged like a fine wine, much like we imagine the Hawaiian shirt he wore in The Descendants has done.

The whole vibe of this movie is just on point, including the wardrobe. Although given the fact it was filmed on location in Hawaii, would it just be called a shirt?

Romeo + Juliet

We’ll leave it to the scholars whether or not William Shakespeare’s classic love story would have increased its longevity if Hawaiian shirts were incorporated into the script. All we will say however is, would it hurt?

Looking at Leonardo DiCaprio effortlessly donning a loose cut Hawaiian shirt in this modern retelling shows what could have been. But soft, what light through yonder shirt breaks?

Raising Arizona

Can we just talk about Nicholas Cage for a second? The man is truly one in a million, and no one else really does it like he does it.

Take the Coen brothers classic Raising Arizona, for example. He may well have been an ex-con who had no problem with kidnapping, you can’t help but love his hyperactive performance.

While his character’s antics in the movie aren’t exactly something we can condone, you have to admit he looked pretty fantastic in the mug shots

Weekend at Bernie’s

Do you want to know the real reason the two young insurance brokers in this bonkers 80s comedy got away with moving a dead body around everywhere? Most people were too distracted by the blinding light of Andrew McCarthy’s Hawaiian shirt to really notice.

Again just to clarify however, this is not an endorsement of the incredibly shady antics of these movie characters. All we are trying to say is that they looked damn good in the process.


Another honourable mention goes to 2011’s Rango, if for no other reason than backing up our point about cool Hawaiian shirts looking good on anyone. We include lizards when we say that, and there aren’t many other items of clothing that can make that claim.

Honorable mention – Magnum PI

More moustache than man, it would be wrong of us to exclude Tom Selleck from this list. He became one of the most iconic TV characters of the 80s whilst wearing cool Hawaiian shirts, and he reminded the world that it was about time they came back in style (not that they were ever out of it).

Without going as far as saying our shirts are lizard-friendly, we reckon you’ll find something you like on our website. We’ve worked with countless brands to create eco-friendly merch that doesn’t end up in the trash, so check out our full offering here.