Hawaiian Shirts for Men: Style, Culture, and History

Mens Hawaiian shirts are lively, comfortable, and a vacation staple. They’re also part of the islands’ history and culture and represent Hawaii’s contributions to the US.

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I love Hawaii. I love the beaches, the water, the trees. I love the sentimental military culture. 

To be honest, though, I’m not usually into spam or giving pineapple the savory treatment. However, I fully enjoy such dishes when I’m in Hawaii. Either they taste better there than they do on the continent, or I just enjoy full immersion. When in Rome, as they say.

For me, Hawaiian shirts for men were always the sartorial equivalent of a Honolulu-style chicken pineapple bowl. I don’t often wear them when I’m not on the islands, but they delight me to no end when I am.

Recently, though, I realized that there are really chic and cool ways to style them in the summer or even in spring. Plus, very few garments have so much culture and history around them the way these silky tops do.

Hawaiian Shirt Pattern and Materials: What Makes It Aloha?

What exactly is a Hawaiian shirt, also known as an aloha shirt? Essentially, it’s a button-up, short-sleeved shirt that originated in its namesake state.

It’s often made from silk, cotton, a silk-cotton blend, or silk-like materials like rayon. These garments are to be lightweight, breathable, and comfortable under the island sun. 

Relatedly, they have a camp-style collar. This means the collar is flat, open, and sewn right into the body of the shirt without a collar band. It’s not meant to stand up or be closed with a tie, like a more formal collar.


Different Hawaiian shirt patterns are an important feature that gives it a distinctive personality. 

Traditionally, the prints could include quilt-like designs, florals, or traditional Hawaiian patterns known as tapa designs. For centuries, artists have incorporated Tapa designs into art on many Pacific Islands, including those in Australia and Asia.

Modern-day aloha shirts can even include playful designs like hula dancers, tropical cocktails, palm trees, and surfing motifs.

Men traditionally wear these lively tops untucked and as a business casual shirt.

Hawaiian Shirts for Men: Origins

The true origins of Hawaiian shirts are highly contested, though they originated in the ‘20s or ‘30s. However, the truth may exist somewhere in the middle of the competing stories. Or, like so many good ideas, it could’ve coincidentally happened to some degree through different proprietors.

An important part of Hawaiian culture and history is immigration from Asia. More precisely, the current Asian American population. For example, the first Japanese immigrants came to the islands in 1885 and now make up 14% of the population. These Asian immigrants labored in the pineapple and sugarcane farmsteads.

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One story is about a local Japanese woman who decided to make shirts using her kimono fabric and create the aloha prototypes.

This woman may or may not have known a shirtmaker named Koichiro Miyamoto. He ran a tailoring business called Musa-Shiya Shoten. As Musa-Shiya, the Shirtmaker, Miyamoto would place the first ad for Hawaiian shirts in the newspapers.

However, the first person to trademark the term “Aloha Shirt” was, supposedly, Chinese merchant Ellery Chun. Chun ran King-Smith Clothiers in Waikiki. He was inspired by young local boys. Many wore Japanese challis shirts and similar styles, which were popular among the local Filipino community.

It’s likely Chen was at least the first person to mass-produce Hawaiian shirts for the market.

The shirt style became a hit on the mainland in the 1930s. If you remember history class, we were well into The Great Depression. It seems the populace needed some optimistic aesthetics. 

And hey, the American mainland always turned to Hawaii when they needed cheering up.

Hawaiian Shirt Style: A Sartorial History

Did you know that office casual Fridays originated because of the Hawaiian shirt? They were originally called Aloha Fridays. Many professional spaces emulated the Hawaiian islands’ business casual attire to celebrate the work week’s end.

The bright colors and floral designs went against the traditional masculine aesthetic at the time. So, how did the Aloha style become so popular?

Casual 6 David Wearing a matching floral setCasual 6 David Wearing a matching floral set

The original influencers are movie stars and the wealthy. 

John Barrymore commissioned Musa-Shiya, the Shirtmaker, to make him a custom shirt made out of a Japanese Kabe Crepe fabric. Shirley Temple also patronized Musa-Shiya in the 1930s.

The only people who could visit Hawaii in the ‘30s were rich men. So, this made the look aspirational. If you could wear an Aloha shirt, for a second, pretend to be one of the guys untouched by The Great Depression.

Vintage Aloha Shirt: Past Style Icons

Vintage Hawaiian shirts are actually my favorite. They seem more authentic, have a story, and don’t have the more novelty-focused design sensibilities that many modern pieces do.


One of the most famous early instances of a style icon donning the Aloha top is Elvis Presley in Blue Hawaii.

First, I’d like to point out how much of the style from that era is back, including the shorter shorts. Second, his shirt in this movie and on the album cover is one of his many iconic looks.

Around this time, overly tropical prints became corny. Fashion brand Shaheen gave the Hawaiian shirt a glow-up, incorporating more abstract and artistic motifs.

Shaheen provided Elvis with his Blue Hawaii shirt, which may arguably be the most famous Aloha shirt in pop culture.

Bing Crosby

Next up, we’ve got Bing Crosby. This angel-voiced crooner was the ultimate everyman and hometown hero.

However, his sense of style was always a bit eccentric. He never knew how to match or complement, and his clothes were scruffy. But he seemed to have fun with them. It’s this sense of fun that makes it unsurprising that he advocated for Hawaiian shirts.

In fact, his combination of Hawaiian, loose-fit trousers, and a classic hat look natural together and on him. It has that effortless vacation vibe that these shirts are perfect for.

Frank Sinatra

Frank Sinatra sported his Hawaiian shirt the same way he sported his suits.

With his fedora and dress trousers, he made it look classy and cosmopolitan.

Tom Selleck

Since Magnum PI took place in Hawaii, there’s no shortage of ways Tom Selleck styled a Hawaiian shirt.

He pulled from a well of light wash jeans, boat shoes, swim shorts, army shirts, and other ‘80s mainstays. 

Brad Pitt

Though Brad Pitt is hardly a past icon, I want to highlight his style in Once Upon a Time in Hollywood. Even though it’s a contemporary movie, it takes place in the ‘late ‘60s. 

Clifford Booth’s style (Pitt’s character) represents that shaggy ‘70s golden boy look akin to Robert Redford.

He wears an open Hawaiian shirt with jeans and a Western belt. It’s like an amalgamation of different kinds of American and Americana fashions. It definitely has an undeniable cool factor about it.

How To Wear a Hawaiian Shirt Today: Hawaiian Shirt Outfits

Here are some Hawaiian shirt outfits. Hopefully, they’ll help you figure out how to wear a Hawaiian shirt in a way that’s right for you.

I like the way actor James Marsters wears his Aloha shirt here because of how everyman it is. It’s essentially a T-shirt and jeans with a pop (that isn’t too loud).

Adding a layer over your Hawaiian shirt is a good way to make it more subtle. Instead of being the star of the show, it’s simply an accent.

Wearing a brightly-colored Hawaiian with shorts during the summer is arguably its most natural habitat.

Actor Ryan Gosling looks chic with his vivid-hued Hawaiian. The broken suit adds class without being too stuffy.

National Hawaiian Shirt Day

Did you know that the third Friday of August is National Hawaiian Shirt Day? This is because Hawaii officially became a US state on August 21, 1959.

Sure, the islands had been supplying the mainland with Hawaiian shirts for decades prior. However, this exchange really symbolizes the relationship the two have had since Hawaii became a US territory in 1898.

Hawaii held a referendum, and 93% of voters approved the switch from territory to state.

Again, we’ve always turned to these islands for solace in dark times. Even before The Great Depression, Hawaiian music became popular during World War I. I maintain that the ukulele has one of the most naturally optimistic sounds an instrument can make. 

Ultimately, this day celebrates this and all of the important contributions the state has made to the US.

Conclusion: Are Hawaiian Shirts Offensive?

You may be wondering — are Hawaiian shirts offensive?

I think they aren’t. Moreover, there isn’t a sense of exclusivity regarding who gets to wear it in the greater imagination. Remember that the shirt is a mixed heritage product meant for an American audience.

Native Hawaiians may be more offended if one wore a traditional Polynesian headdress, facial makeup, and tattoos in an inappropriate way.

The Hawaiian shirt itself is safely part of American sartorial traditions as a whole.

Now you know that you can style Hawaiian shirts for men in several cool ways. You also know the history behind it. As such, you might be tempted to add one or a few to your closet.

Are you a fan of Hawaiian shirts? If not, would you give them a chance? Let’s start a conversation in the comments!

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