Summer Travel Quest #19

Find the Perfect Hawaiian Shirt

The right garment has the power to influence your life in profound ways. The proof? Our intrepid traveler’s experience in the Hawaiian Islands.
by Dave Seminara
Dave Seminara is a journalist and former diplomat based in Chicago. In addition to Hawaiian shirts, he is also partial to dashboard hula girls, tiki masks and Cook Kwee's Maui Cookies. 

No one’s going to stop you at the airport and demand proof that you’ve purchased one before allowing you to go home, but on the Hawaiian Islands men are drawn to Hawaiian shirts like mice to cheese. On a recent trip to Maui I became obsessed with finding the perfect Hawaiian shirt, so much so that I spent almost as much time in dressing rooms as I did on the beach.

According to Dale Hope, author of "The Aloha Shirt: Spirit of the Islands," about the history of Hawaiian shirts, the garment was first sold by a Japanese immigrant at the Musashiya fabric store in Honolulu in 1935. The early shirts were made of the same fabric used in Japanese kimonos; priced at just 95 cents, they were marketed as souvenirs.

Servicemen who had done tours on bases in Hawaii helped make them popular on the mainland in the 1940s, but in the decades since they’ve dipped in and out of fashion. According to a recent story in the Wall Street Journal, Hawaiian shirts are now hotter than ever, with a host of high-end designers like Prada, Tommy Hilfiger and Saint Laurent introducing their versions of the iconic shirt in recent years.


If you can’t make it to Hawaii, check out, which specializes in Aloha shirts made in Hawaii.

There are dozens, perhaps hundreds, of places to buy Hawaiian shirts on Maui.  You can find them at the ubiquitous ABC convenience stores, the Whaler’s General Stores, at Hilo Hattie, a kind of Hawaiian department store, in roadside stalls, and even at Costco and Wal-Mart. I wanted one made in Hawaii, which narrows the field a bit, but not as much as one might expect. Nearly every garment in my closet was made somewhere in Asia, but I learned that there are still dozens of companies making them in the Aloha State, including the Tori Richard and Duke Kahanamoku brands, to name just a few.

I imagined my ideal Hawaiian shirt to have an unmistakably Polynesian vibe and I wanted it to be colorful, but not so obnoxious that I’d be embarrassed to wear it in Chicago, where I live. I grew up watching "Magnum P.I.," and, even if I could never duplicate Tom Selleck’s bushy mustache or rugged good looks, I could at least buy a cool Hawaiian shirt like the kind he used to wear on the show. I tried on dozens of shirts in shops all around the island during the first week of our trip. I learned that locals call them “Aloha shirts,” but I couldn’t settle on the shirt to bring back to the mainland. Some were too expensive, the fabric in others felt shoddy, and in many cases, I looked like a buffoon—the tourist in the garish Hawaiian shirt who couldn’t quite pull off the look.

The Quest Goes On

Two nights before we were due to leave Maui, I was still Aloha-shirtless and felt like time was running out. We were going to a luau at the Grand Wailea Hotel that night, and what self-respecting tourist shows up at a luau with no Aloha shirt? I’d already found a pair of sweet, vintage-style Hawaiian shirts for my sons, Leo, 6, and James, 4, and the thought crossed my mind that we could hit the tourist trifecta by turning up in matching shirts. But alas, I couldn’t find acceptably cool, matching shirts in the three sizes we needed.

After several unsuccessful shopping trips, my wife lost patience with my quest.

“We’re in Maui and you want to spend all your time looking for Hawaiian shirts?” she asked. “You can count me out.”

So the day after suffering the indignity of going to the luau sans Aloha shirt, I set out alone to find my shirt. I was tempted by three shirts at the Whaler’s General Store in Wailea, a black number with big pineapples, an understated white shirt with palm trees, and a brown, flowery affair, but couldn’t decide which one to buy. I tried them on, took selfies and then texted them to my wife. But alas, she was not impressed.

“You can do better,” she replied.  

Sensing my desperation, she offered to accompany me to Hilo Hattie’s, a large chain store that I’d been told had a huge selection of Aloha shirts, that night. With her help, I settled on a faded, blue-green cotton/polyester blend Aloha shirt with palm trees made by Hilo Hattie. I can’t tell you exactly what set this shirt apart from the dozens of others I had tried on, but it simply felt right. And my wife didn’t laugh when she saw me in it.

The Spirit of Aloha

We returned to Chicago in the middle of the most brutal winter in recent memory. After spending 10 days in paradise, our drafty apartment seemed even more depressing and inadequate than it had before the trip. But whenever I needed a little lift I’d put on my Aloha shirt, and it never failed to boost my spirits. There is, I found out, a very good reason why Hawaiian shirts are a popular souvenir. You really are bringing a little of the spirit, some of the magic of the Aloha State with you in bringing one of these beauties back to the mainland.

When you wear one, even on a brutally cold February day in the Midwest, it feels appropriate to cut out of work a bit early and indulge in a Mai Tai or three. Have you ever been cut off in traffic by someone wearing a Hawaiian shirt? Ever been fired by someone wearing a Hawaiian shirt? Of course you haven’t, and there’s a good reason for that. When I wear my shirt, I feel that I’m being perceived differently. People assume that I’m friendly and approachable, someone who doesn’t take himself or anything else too seriously.

And that, my friends, is a souvenir worth obsessing over.


Dave Seminara is a journalist and former diplomat based in Chicago. In addition to Hawaiian shirts, he is also partial to dashboard hula girls, tiki masks and Cook Kwee's Maui Cookies. 



17) Walk the Longest Pier on the West Coast

18) Touch a Dinosaur Bone in the Wild

19) Find the Perfect Hawaiian Shirt

20) Drink in an Ice Vault

21) Take Home a Pennsylvania Dutch Quilt

>> All 99 Summer Travel Quests


Use the hashtag #99SummerQuests to share your own summer travels, and follow along with us at @MapQuest and Instagram.

The author and his sons in their Hawaiian shirts
The author and his sons in their Hawaiian shirts