Man wearing Hawaiian shirt

How to Wear the Hawaiian Shirt: The Rebirth of a Classic Vacation style is finally reborn

Not long ago, the Hawaiian shirt was stitched deep into the fabric of boring dad style. The Hawaiian shirt screamed depressed Friday office style not one of the best trends in fashion. For some reason, the sartorial gods descended from their golden throne to bring the Hawaiian shirt back to us. The Hawaiian shirt is reborn.

The Hawaiian shirt is everywhere now. Pretty much every celebrity and men’s fashion icon is sporting it. There’s a good reason too. While not every trend is something we support here at the GentleManual, this one is a keeper. I think we can all admit that even though the Hawaiian shirt might have seemed like a sad attempt to recapture that sense of vacation easygoingness, we all secretly had some love for them. There’s no way you can watch Magnum P.I. and not want one of your own. This is only amplified when you find yourself falling into a sea of men in navy and black.

Before you get too excited, there are some guidelines to follow. We’ll break down everything you need to know.

Table of Contents

A Laid Back History


The Hawaiian shirt was first created by Chōtarō Miyamoto in his store in Honolulu Hawaii. A few decades later a man named Ellery Chan modernized the look and sold it en-mass. Soon the Hawaiian shirt was all over the islands. When troops stationed in Hawaii during World War 2 returned home, they brought the look back with them. This rocked men’s fashion and made Hawaii a mecca for all things vacation wear.

In the 60’s the shirt gained even further traction when businesses on the island started to adopt the style during the hot summer months. Soon Aloha Fridays became a popular trend and swept across the ocean and to the mainland. This became what we know as casual Fridays. After that, the Hawaiian shirt became tied to stuffy office wear to the detriment of men’s style everywhere.

Recently, designers have started to invoke this classic style and bring it back to the modern era.

The Commandments of Wearing Hawaiian Shirts (ignore at your peril)

While the Hawaiian shirt has risen like a phoenix back into menswear, the stigma of the old days hasn’t entirely been shaken. If you’re going to rock this look, there are some rules to follow.

The Fit is Always Everything


The fit is everything. The oversized trend might be working its tendrils into everything but this isn’t one of those things. A baggy Hawaiian shirt is going to leave you looking like your dad’s boss not like a rock star. Get something that is form fitting and tailored to your body. If you’re a bigger guy, this is especially important. The bold prints will keep you looking slim while the proper fit won’t have you swimming in fabric.

Island Confidence


The Hawaiian shirt isn’t boring anymore. It’s all about being loud and standing out. No matter how great the shirt looks, it won’t work if you look petrified in it. If confidence doesn’t come easily to you, don’t worry. There are a few things you can do to make it work for you either way.

Downplaying the Hawaiian shirt might be just what you need to rock it. Instead of sporting it front and center, mute it by layering under a solid colored jacket. The simple outfit will still allow your shirt to express itself without being in your face. The second option is choosing shirts with more low-key designs. Not everyone wants a whole island landscape on their shirt. Classic flower patterns and muted colors still capture everything that’s great about the Hawaiian shirt.

Styling the Right Way


We’ve covered above what to do if you want to keep the style lowkey but for those ready to dive headfirst into the look, go wild. The Hawaiian shirt is fun so take it wherever you want to go. Change up the classic materials or go for a collarless shirt. Pair with a cool pair of jeans or even a matching print pair of shorts and rock festival style every day. Keep things lively with some accessories like a silver ring or necklace.

Our Picks

Here are some over the very best Hawaain shirt brands on the market. We’ve covered picks for every look so you can get a Hawaiian shirt for cheap while still nailing the look.

The Classic

Lu’au Hawaiian Shirt


Hawaiian Shirt Mens Flower Leaf Beach Aloha Party Casual Holiday Short Sleeve

  • High “Fits as expected” ratio
  • Matching Front pocket
  • 100% Polyester drapes like silk
  • Bright Vibrant Colors

All Saints makes some of the best menswear out there. Their Lu’au shirt hits old the right old-timey notes while still being as cool as anything on the market. The muted pink is perfect for balancing trendy and traditional.

The Reserved

Palm Tree Shirt


LA LEELA Men’s Hawaiian Casual Aloha Button Down Shirts

  • Soft smooth lightweight non sheer fabric
  • good for light travel and no see through material.

Black and white are the two basic colors for a reason. They go with literally everything. The lowkey palm tree design reminds you that you are indeed wearing a Hawaiian shirt but is so reserved it wouldn’t be out of place in any setting. This black Hawaiian shirt is a no-brainer. Go get it.

The Versatile

Short-Sleeve Shirt in Blue Floral


J.Crew Short Sleeve Printed Rayon Faille Camp Collar

  • 100% Rayon
  • Cut with a regular fit.
  • Short sleeves.

J-Crew is largely responsible for getting men interested in fashion. Their blue floral shirt is perfect for someone looking for a shirt to rock on the weekend but one that also looks fantastic with a blazer. The print is bold while the colors are classic, giving you the best of both worlds.

The Trendy

Electric Toucan Rayon Shirt
Ready to throw caution to the wind? The electric toucan shirt from Urban Outfitters will definitely draw all attention to you. The print is fun without overdoing it and the colors are lively and eye-catching.

Our Look

Hawaiian Shirt Flat Lay


While I can’t say for certain if the Hawaiian shirt will be here to stay (I hope it does), it’s definitely the trend of the moment. Good fits, exciting colors and interesting designs all make this one worth getting. Make sure to have fun with it and we might just save it from returning back to the fathoms of boring office style.

How are you having fun with your style? Let us know below!

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