Famous People Who Rocked the Hawaiian Shirt (and Why You Should Too)

Written by James Hamilton

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Posted on February 02 2025

Hawaiian shirts—love them or hate them, they’ve made a lasting impact in pop culture. What was once the uniform of island tourists and dad jokes has now become a symbol of effortless cool. And guess what? Some of the most iconic people in history have worn them with absolute swagger.

If you’re wondering whether you can pull off a bold, bright, and unapologetically loud Hawaiian shirt (like the ones from CPTN Shirts—wink, wink), take inspiration from these legends who did it first.

1. Elvis Presley – The King of Aloha

When you think of Hawaiian shirts, Elvis in Blue Hawaii (1961) is probably the first image that comes to mind. The King of Rock and Roll cemented the aloha shirt as a fashion staple when he crooned his way through paradise, making it look both stylish and rebellious. Want to channel Elvis? Go for a bold red or blue floral print and add a bit of hip swivel.

2. Tom Selleck – The Magnum P.I. Look

If there’s one man who made the Hawaiian shirt look rugged and effortlessly cool, it’s Tom Selleck. Magnum P.I. wasn’t just about solving mysteries in a Ferrari—it was about that signature red Hawaiian shirt with tigers and palm trees. Even decades later, it’s still an iconic fashion statement. The secret? Selleck wore it with confidence, a killer mustache, and a tan.

3. Hunter S. Thompson – Gonzo Journalism Meets Loud Fashion

The legendary writer and journalist wasn’t just known for his wild stories; his style was just as chaotic. Often spotted in Hawaiian shirts, aviator sunglasses, and a cigarette dangling from his lips, Hunter S. Thompson made the shirt part of his larger-than-life persona. His philosophy? If you’re going to go bold, commit to it.

4. Tony Montana – Say Hello to My Little Shirt

Al Pacino’s Tony Montana in Scarface showed the world that Hawaiian shirts weren’t just for vacations. The bright prints, paired with that unmistakable gangster swagger, made it a power move. If you want to own a room, take a cue from Tony—pair a Cuban-style Hawaiian shirt with some serious attitude (minus the whole drug empire thing).

5. Leonardo DiCaprio – The Romeo + Juliet Revolution

Before Leo was trading stocks on Wall Street or freezing in the Atlantic, he was the ultimate ‘90s heartthrob in Romeo + Juliet (1996). His modernized Romeo rocked an open Hawaiian shirt with a gun holster, making Shakespeare cool again. The takeaway? Hawaiian shirts aren’t just for beach trips; they can be straight-up cinematic.

6. Jim Carrey – Loud Shirt, Louder Personality

Ace Ventura: Pet Detective (1994) gave us one of the most eccentric characters of the ‘90s, complete with an over-the-top personality and an equally wild wardrobe. Jim Carrey’s Hawaiian shirts in the film were a reflection of his unpredictable energy. Moral of the story? A Hawaiian shirt is a statement—wear it like you mean it.

7. Brad Pitt – The Fight Club Mismatch

In Fight Club (1999), Brad Pitt’s Tyler Durden turned chaos into a fashion statement. Mismatched prints, oversized sunglasses, and, of course, a beat-up Hawaiian shirt became the look of anarchy. If you ever wanted to look like you don’t care but still somehow be effortlessly stylish, this is your template.

8. Jeff Goldblum – The King of Quirk

Goldblum is proof that age doesn’t matter when it comes to pulling off a Hawaiian shirt. Whether on the red carpet or just strolling the streets, he wears them with a mix of charm, intelligence, and just enough quirk to make it work. His secret? Tailored fits and killer accessories.

9. Matthew McConaughey – Alright, Alright, Alright

McConaughey in The Beach Bum (2019) is the embodiment of laid-back, don’t-give-a-damn Hawaiian shirt energy. Whether he’s chilling in a convertible or giving motivational speeches, he wears the shirt like a second skin. The key takeaway? A Hawaiian shirt is best worn with an easygoing attitude and a bit of Southern charm.

10. Johnny Depp – The Ultimate Eccentric

From Fear and Loathing in Las Vegas to real life, Johnny Depp has always been a fan of loud, printed shirts. He proves that a Hawaiian shirt isn’t just casual—it can be part of a larger rockstar-meets-gypsy aesthetic. If you want to channel Depp, add some accessories—rings, bracelets, and a little mystery.

Why You Should Wear a Hawaiian Shirt Today

  • Confidence is key – Every single person on this list rocked their Hawaiian shirt with zero hesitation.
  • They work for every occasion – Beach party? Yes. Casual Friday? Absolutely. Running a multi-million-dollar smuggling operation? If that’s your thing.
  • It’s impossible to be in a bad mood in one – Try it. Hawaiian shirts radiate good vibes.

So, whether you’re hosting a podcast, heading to brunch, or just want to make a statement, grab yourself a Hawaiian shirt. And if you want the best, well… you know where to look (CPTN Shirts, obviously).

Now, go out there and rock the aloha look like a legend.

4o

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