How to Find the Perfect Aloha Hawaiian Shirt

VINTAGE ALOHAThere is nothing like a perfectly draped, classically patterned Aloha shirt to put you in an Hawaiian state of mind.

David Bailey has been collecting and selling vintage Hawaiian shirts since 1980 and he now has the world’s largest collection of 15,000 Aloha shirts at his Bailey’s Antiques Store in a pink stucco building tucked away in suburban Honolulu well away from the overpriced tourist strip in Waikiki.

It is well worth making the effort to get here both for a trip down memory lane and to get some real gems in any price range.  You’ll also discover just how Aloha shirts first became popular and what makes them so appealing.


For centuries there were no shirts in Hawaii, much less brightly colored Aloha shirts. The original Polynesian Hawaiians wore tapa or bark cloth with simple geometric designs for special occasions. Then the missionaries introduced solid colored work shirts for men and long shapeless dresses called muumuus for women.

The modern Aloha shirt was devised in the early 1930s by native Hawaiian Ellery Chun who graduated with an economics degree from Yale in 1931. He transformed a Chinese dry goods shop, King-Smith Clothiers and Dry Goods, in Waikiki into the first producer of Hawaiian shirts. Chun had his tailors sew brightly colored shirts for tourists out of old Japanese kimono fabrics leftover in stock. The Honolulu Advertiser newspaper was quick to coin the term Aloha shirt to describe Chun’s fashionable creation and he trademarked the name.

Local residents, especially surfers, and tourists descended on Chun’s store and bought every shirt he had. Within years, major designer labels sprang up all over Hawaii and began manufacturing and selling Aloha shirts en masse. Many Hawaiian companies today use mass-produced aloha shirt designs for employee uniforms.


Hand-painted Aloha shirts

After World War II, servicemen returned to the United States from Asia and the Pacific islands with aloha shirts made in Hawaii since the 1930s. Tourists began flocking to Hawaii in the 1950s as faster airplanes allowed for easier travel and the former U.S. territory became a state in 1959. Everybody wanted an aloha shirt to take home.

Alfred Shaheen, a textile manufacturer, revolutionized the garment industry in postwar Hawaii by designing, printing and producing aloha shirts and other ready-to-wear items under one roof. The tropical-print shirts for men became standard and sometimes tacky souvenirs for travelers, but Shaheen raised the garments to the level of high fashion with artistic prints, high-grade materials and quality construction.  Tori Richard was a prominent designer of these shirts, establishing a business in Honolulu in 1956. Elvis Presley wore a Shaheen-designed red aloha shirt featured on the album cover for the Blue Hawaii soundtrack in 1961 while Tom Selleck’s Bird Airbrush shirt from th Magnum PI TV series is now in the Smithsonian Institution. Frank Sinatra, Big Crosby and even presidents Harry S. Truman and Dwight D. Eisenhower were huge fans.


The key elements of a perfect Aloha shirt

A lot of modern Hawaiian shirts are now fabricated in Asia, which makes Hawaiian-fabricated vintage shirts all the more appealing. They are also more carefully crafted with double stitching and often with buttons made from coconut wood.

The key to the perfect shirt is in its draping which is achieved with the finest silk or rayon material, most of which comes from Japan.


David Bailey wearing a replica Halei Hawaii shirt

Many of the older vintage shirts are adorned with traditional Polynesian quilt and tapa designs and simple floral patterns in muted colours. As designs were developed for the tourist market, swaying palms and hula dancers became popular motifs. More recent designs can be brighter with any number of elements such as cars, ukuleles, or drinks arranged in a pattern.

What you will find at Baileys

Bailey’s has something for everyone with several thousand modern and replica vintage shirts priced as low as $3.99 to hand-painted shirts that can sell for as much as $8000 each.

The shirts are organized according to vintage.

There are 2000 shirts under $10 and 5000 shirts under $20. There are also about 1000 shirts from the 1960s and 1970s and about 800 from the 1940s and 1950s. Some of the finest vintage shirts sell on average for about $1000.

Collectors should look out for specialty local Hawaiian designers such as Reyn Spooner, Sig Zanes, Tommy Bahamas, and Hale Hawaii.

Anthony Bourdain visited the store about eight years ago while he was researching foodie stories down the street and ended up filming in Bailey’s Antiques. He bought an original Halei Hawaii shirt for $2500 but David Bailey also has copies of the same shirt for $89.

Jimmy Buffet has spent more than $20,000 in the store and Nicolas Cage and Peter Fonda have also dropped big bucks here.

Luckily for the regular punter, David Bailey bought the building about 17 years ago where Bailey’s Antiques is now located. If he had stayed in Waikiki, where the rents have quadrupled, none of us would be able to buy the gems that are in this store for the prices that he charges.

And for those who are into memorabilia, there is lots to keep you entertained from fridge magnets and bobble heads for your car dashboard to reproduction vintage postcards.

But don’t let them distract you from the real gems that always carry the spirit of Aloha.  Happy holidays.


Your say

If you have any great suggestions for other authentic Hawaiian made products, I’d love to hear from you.



Bailey’s Antiques in Honolulu

Baileys Antique Store

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Baileys Antique Store 21.283616, -157.822380

Sue Gough Henly

Sue Gough Henly is award-winning travel writer and photographer whose bi-line has appeared in The New York Times, Travel & Leisure, The Guardian, The Toronto Star and all the major Australian publications. Her travel blog, Genuine Journeys, is full of insider tips on the best places for authentic experiences and luxury splurges. She is also the author of Australia’s Best Places travel app. When she doesn’t have sand between her toes or a pack on her back, she writes about food, wine and culture.

2 comments to How to Find the Perfect Aloha Hawaiian Shirt

  • Tobias Armstrong  says:

    I’d never really thought about quilts as a potential souvenir. It makes sense that Hawaiian shirts would be based on Polynesian quilts though, I just hadn’t thought about it before. I love that there is such a variety of souvenir options that you can start to get creative in what you’re looking for and not feel like you’re going to pick up the same thing that everyone else has. Thanks for sharing!

    • Sue Gough Henly  says:

      You’re welcome. I hope you found yourself some cool vintage Hawaiian shirts!

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