David Bailey. Photos by Aaron Yoshino

Meet The Man With The World's Largest Collection Of Hawaiian Shirts

BY Austen Rosenfeld | Mon. May 12, 2014 | 12:00 AM | A La Mode
They were hip in the ‘60s when Elvis crooned over a ukulele in Blue Hawaii. Then in 1983 when Tony Montana delivered his unforgettable, “say hello to my little friend.” Raoul Duke rocked one through the desert in Fear and Loathing In Las Vegas and they made a comeback in the ‘90s with Jim Carrey in Ace Ventura. Hawaiian shirts go in and out of style, but they never go away. Now, the floral prints are back, hitting runways everywhere from Mother of Pearl to Dries Van Noten to our own Opening Ceremony X Elvis collection. In honor of island fever, we found the man who knows more about Aloha shirts than anyone. Meet David Bailey, owner of the largest collection of Hawaiian shirts––over 15,000!––in the world.

In case you’re curious about the origin story: early Hawaiian shirts were inspired by the geometric designs of traditional Polynesian clothing called tapa cloth­­—malo loincloth for men and the pa’u skirt for women. That, mixed with the western sewing techniques of foreign settlers and the missionaries’ interest in “modest” ways of dressing, created the precursor to the Aloha shirt as we know it. The modern Hawaiian shirt (with its palm tree, pineapple, and surfer motifs) became commercial in the 1930s, spreading with tourism and the opening of the Royal Hawaiian Hotel on Waikiki.

On a recent visit to Bailey’s Antiques and Aloha Shirts, David’s vintage emporium in Honolulu, I chatted with the expert about Elvis, Honolulu, and, of course, Hawaiian shirts.

AUSTEN ROSENFELD: How did you start your collection?
DAVID BAILEY: Well, it was the late '70s and I was a hang glider in Santa Barbara and I had an accident… I fell over 1,000 feet. I’m the only one who can say that and live to talk about it. At that point, I quit and I had a job in a small store in Santa Barbara selling jewelry. I started collecting Hawaiian shirts when they were really cheap and once I had 1,000 I opened up a store.

Do you have a favorite Hawaiian print?
Oh, no. For me it’s basically a commodity now. I like florals. I usually take a shirt and wear it a few years, then exchange it out... I’m always open to selling the shirt off my back. I like to call it wearable art. It’s a good investment, better than the stocks I pick which all uniformly go down. But the shirts tend to go up.

What are some well-known Hawaiian prints or artists?
Alfred Shaheen is well known. Right now, what is called the hand-painted back panel shirts, by McGregor and Catalina, are very high-end. There are a couple artists [whom I sell here]: one is Eugene Savage [and] the other is Frank McKintosh, who designed the menus for the Lurline ships that used to come [to Hawaii].

How can you tell an original from a replica?
The best three indicators of a pre-1960s shirt are horizontal buttonholes, French, or flat, seam on sides and around armpits, and an old label. Rayon is most valuable, although shirts were also made from cotton, nylon, and silk in the '40s and '50s. Laser technology since about 1990 has allowed almost perfect replicas, which changed the industry, as it is cheaper to copy than to hire an artist.

How did Elvis change the way Hawaiian shirts were perceived? Are you an Elvis fan?
It was about 60 years ago when I was at a friend's house and he had a 45 rpm of Elvis singing "Heartbreak Hotel," which we played until his older brother threatened to break it. We were about ten. I would say his movies put some positive momentum into all things Hawaiian, but Tom Selleck had a larger positive effect on the Hawaiian shirt industry.

Who would you like to see wearing your Hawaiian shirts?
We sold a bunch of shirts, over $20,000 [worth], to Jimmy Buffett, who wore our most expensive shirt when he performed. Over $10,000 to Peter Fonda and Nicolas Cage, each. We get a lot of celebrities. We never know who’s going to come in. We had Adam Sandler. Steve Martin.

In your opinion, what should a Hawaiian shirt be worn with?
I wear them with shorts all the time. They can be worn with blue jeans. White pants, black pants. Anything. The younger generation and [the] Internet have made it clear that creativity is actually enhanced [when] people take the noose off their necks. I never understood suits. I don’t even own a tie. They’re creepy, actually, if you think about it. They turn people into little robot ants. [When] you wear a Hawaiian shirt it allows you to express yourself.

Has Honolulu changed since you opened the shop?
I first got to Honolulu in 1965 and there are a lot more cars, people, and concrete since then.

Do you surf?

I am pretty good at body surfing but do not surf.