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Three Hawaiian-Shirt-Clad Boomers on Millennials Stealing Their Look

By several accounts, 2018 was the Summer of Sleaze, headlined by Justin Bieber and his arsenal of garish aloha shirts (or, as mainlanders know it, the “Hawaiian” shirt) that made him look like your best friend’s semi-flaky South Beach cocaine dealer, circa 1982. Bieber’s fondness for a particularly, er, loud palette of shirts may put him on the extreme end of the aesthetic, but since celeb style tends to inform consumer trends, Bieber’s fits (or something like them) can now be seen on a male mannequin near you, whether it be via the dirt-cheap fast-fashion retailer H&M or timeless designer favorite Louis Vuitton.

In other words: Aloha shirts are hip for real, whether you’re going lowbrow or highbrow. And millennials in particular can’t seem to get enough of them.

This is an odd but not unexpected turn of events for David Bailey, who has worn an aloha shirt every single day for the last 30 years. Actually, scratch that: “I’ve missed maybe three days,” he says, before cracking a laugh. Bailey, 73, is perhaps the greatest hunter-gatherer of aloha shirts in America, having amassed an estimated 15,000 in his cocoon of a shop, Bailey’s Antiques and Aloha Shirts, which is a 10-minute drive from tourist-thronged Waikiki Beach in Honolulu.

Dig into the endless shelves and spirals of clothing and you might stumble across rarities like a hand-painted vintage rayon shirt from the 1960s, or perhaps a modern reproduction of a classic design worn by Frank Sinatra in From Here to Eternity. Some shirts go for under $5, while many others have appreciated in value since they first came off the sewing line. Anthony Bourdain dropped $3,000 here in 2008 while taping his travel show No Reservations. King of Margaritaville Jimmy Buffett got one for $5,000. Meanwhile, Nic Cage, never one to be outdone, spent $10,000 on a vintage shirt.

“The thought of wearing just a plain white or blue collared shirt is totally boring,” Bailey explains. “What we’re seeing is people who get into aloha shirts by having one, then five, then 50. Manufacturers I talk to are seeing increased sales everywhere, especially on the East Coast and in Europe. We’ve got Hawaii Five-0 and now Magnum P.I. back on TV, showing off the aloha shirt look. The vibe is ripe.”

How the shirt came to be is a matter of academic debate, but there’s agreement around the idea that it was influenced by the colorful Japanese fabrics that were being imported to Hawaii in the early 20th century, and widely used by Japanese families to sew their own clothing. The brightest, most eye-popping colors and patterns were initially reserved for children and young women, says DeSoto Brown, historian at the Bishop Museum in Honolulu. Chinese businessman Ellery Chun had a major influence in the 1930s when he began producing patterned shirts en masse, and Brown credits teens and other young people for fueling the fad of the aloha shirt as a form of local streetwear, during a time when most Americans were dressing conservatively.

“In the late 1930s, there was a brief moment of Hawaii being very fashionable for very wealthy young mainland people, who were part of what was called ‘café society.’ After Doris Duke built her house here, which got a ton of national publicity, other rich young people started vacationing here, or even buying their own houses,” Brown continues. “They wore alohawear in publicity or news photos, which not only helped spread awareness of it, but also made it desirable for other people to copy.”

That blew up in the 1950s and early 1960s, when Elvis Presley and Sinatra donned aloha shirts in films, and the Polynesian tiki-culture craze swept across the U.S., starting on the West Coast. “By the 1970s, old aloha shirts first got recycled by hippies who were trying to look oddball, to break with the established expectations. By the 1990s, the cliché of the ‘Fabulous ‘50s’ was also in place in American culture, and a small part of that was the old-fashioned-style aloha shirt,” Brown explains.

For many boomer men like Bailey, however, the aloha shirt isn’t a summer fad — it’s a long-lasting love built on an earnest appreciation for the practicality and style of a unique clothing tradition. The shirt represents the ultimate compromise between buttoned-up and laid-back — an alternative to the prim look of the midcentury white-collar man, and later, the Gordon Gekko pretension of the 1980s. And so, while millennials are certainly buying into the beachy-cool vibe of the aloha shirt, we found three men who have fallen in love with the garment exactly because it tries not to be hip. Here’s what they have to say…

David Bailey, 73, Collector of Antiques and Vintage Shirts, Honolulu

I grew up in Ann Arbor, Michigan, but I traveled all around when I was in college, studying as an exchange student in Japan at Waseda University and also at the University of Hawaii. I settled down back in Santa Barbara and ran some jewelry stores — I was trying to sell gold chains. It was a true hand-to-mouth operation, though. My background was more being a collector — whether it was stamps, bugs or miniature Buddhas — and I was just looking for a steady income. One day, I collaborated with an antique shop and put up a single rack of vintage clothes. It wasn’t too long before it was obvious that vintage clothes was a better sell than antiques or gold chains.

I rented a garage for $20 a month and spent a lot of time going to big local swap meets and buying what looked good. After a year, I had a thousand shirts, mostly rayon fabric from the 1960s. The dream was to do a vintage clothing shop in Hawaii, and I found a $1,000 a month storefront on Kalakaua Street. That was 1980. The first year I sold five times what I did in the jewelry business. For the next 20 years, I just went to flea markets before the sun came up. Half the shirts in the store are from that time period. And obviously, it was fun to have first pick of my favorite shirts to wear.

These days, I mostly look at eBay and other sites. What’s been happening more and more is that our early customers are coming back, having outgrown their aloha shirts with age, and we take their shirts and give them other ones. Alongside the repeat customers, we get a lot of tourists, especially Japanese tourists. And we have a number of stores in Australia, Japan and Europe that buy from us wholesale. The prices are ridiculous out there — we’ll sell something for $30, and I’ll find the same shirt resold at $250 in Australia! But I guess that’s not unusual when Louis Vuitton is releasing an aloha shirt, and more and more high-end manufacturers are seeing good business.

The good news is that younger workers know that going to work while wearing a noose around your neck doesn’t help productivity. The idea of casual office wear started here, in Hawaii, with Aloha Fridays as a local social campaign. That’s where Casual Friday comes from. And that’s why I’ve worn an aloha shirt every day for decades. The bad side is that rents have gone to the moon around us in Waikiki Beach. It’s totally corporate here now, with a brand like Tommy Bahama paying $100,000 a month to sell their stuff. The mom-and-pop shops for aloha shirts are all going away, despite the popularity of the shirts themselves.

Eric Peterson, 66, Film Production/Camera Work, L.A.

I have dozens of aloha shirts, and I wear them every single day. It’s my little uniform. You get to my age, it’s nice to have a standard look to lean on, and not have to overthink it. I can’t quite remember where I first noticed the aloha shirt, however. I think as much as anything else, I learned about them by reading Fear and Loathing in Las Vegas and realizing my hero, Hunter S. Thompson, wore them (laughs). I definitely saw them in Los Angeles once I moved here. Growing up on the East Coast, you didn’t see aloha shirts that much.

I really started to get familiar with the shirts when I got a job with Disney on this dinosaur movie, and spent about a year in Polynesia and in Australia. One of our grips wore aloha shirts as his daily uniform. I’m pretty sure I bought my first one when I got back to L.A. But really, much of the buying started around a decade ago, when I discovered eBay as a source for them. I found a few brands that I really liked — my favorite is Reyn Spooner — and I just keep going back.

The favorite design I own is the Japanese crashing wave motif, popularized by the artist Hokusai. They’re very modern looking, almost minimalist. But that’s the thing about aloha shirts: They can look dressy in their own way, especially with the traditional ones that are reverse-printed so that the colors look muted. I saw a guy on the street who had big pineapples on a super vibrant shirt, and I wasn’t even sure if that would qualify as a real aloha shirt. Clearly, the style has defied a single time period. It’s an aesthetic that reinvents itself. But if aloha shirts are back in, well, I haven’t noticed.

I will say, I bought a beautiful one at Bloomingdales in New York City not too long ago. It was expensive, from a high-end trendy label that I can’t recall, but beautiful. Then I saw it on a bartender in a Budweiser commercial, so I guess my taste is vindicated (laughs).

John Carlson, 67, Professor, San Francisco

Honestly, I thought they were out of style now. There was a resurgence of Hawaiian shirts about eight or ten years ago. My daughter and I were at a conference, and we showed up for dinner and a few of the cooler guys had on Hawaiian shirts. My wife told me I should try them on myself, and I thought, Okay, it’s cooler than a golf shirt and way dressier than a T-shirt, so at least it’s versatile. When I traveled across Europe last summer, I took three Hawaiian shirts because I felt like I could fit in anywhere with a collared shirt that had some flair.

I’ve always thought there’s a huge difference between wearing a collared shirt and not. I would never go to a function in a T-shirt. But the Hawaiian shirt gives you such a wide variety of patterns, anywhere from subdued to crazy. I’ve got one that’s just a bunch of WWII bombers! I don’t wear it in public too often, but a shirt like that can tell others about your interests. You can find a pattern of just about anything these days. Admittedly, my favorite is the first one my wife and daughter got me — a floral pattern in dark blues and greens, just a touch classy.

I must’ve really noticed the Hawaiian shirt for the first time in the early 1970s, with a guy who had just moved from Hawaii. It was bizarre to see. It looked like the kind of fabric you’d see on early 1960s furniture. But I thought it was beautiful, too. There was just so much fanfare in that era because it was the first time for many to be able to fly to Hawaii, and the culture affected everything. Actually, on second thought, I must’ve seen the shirt for the first time on the original Hawaii Five-0.

I wear them regularly now — it reflects my lifestyle since I’m basically in retirement. I wouldn’t wear them as a full-time professional. I’m surprised they’re a fad, though. I don’t want to fit in with everyone else, especially if the young tech workers are adopting it! I don’t want to look like the old guy who’s trying to be young, and I especially don’t want to look and talk like a techie.