The Greatest Hawaiian Shirts in Pop Culture History

Some of the most memorable florals from television, film, and beyond.

August 8, 2015
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The Hawaiian shirt is back baby. The shirt that has long languished as the go-to shirt for barbecuing dads, drunk uncles, and big galoots of all kinds has returned to the runway against all odds. H&M, Urban Outfitters, and other major men's retailers are lining their shelves with Hawaiian and floral offerings. Fashionable celebrities have been spotted in tropical print tops. And yes, trend pieces have been written.

Though the Hawaiian shirt is on top today, it has been a roller coaster ride for the tropical print shirt. Few items go in and out of style as rapidly as the Aloha print. The Hawaiian shirt has had moments of pop culture glory and dark days of unstylish infamy. Let's celebrate those Hawaiian high Aloha lows with The Greatest Hawaiian Shirts in Pop Culture History.

Elvis Presley, Blue Hawaii (1961)

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Blue Hawaii and its accompanying soundtrack were huge commercial successes. The film stands as Elvis's highest grossing, and the soundtrack could be found in houses across the country. Like most pop culture phenomena, Blue Hawaii's triumph rode a wave of existing cultural energy. South Seas fever was sweeping the nation at the time. The musical South Pacific, muumuus, pu-pu platters, and other Hawaiian trends became American fascinations after Hawaii was granted statehood in 1959.

World War II veteran Alfred Shaheen saw an opportunity in the America's love affair with Hawaii, and began manufacturing Aloha shirts in a Quonset hut with only four seamstresses. Before Shaheen's work was done, Hawaiian shirts would become the third largest industry in the state. Shaheen's breakthrough with the Hawaiian shirt is also credited with spurring the rise of Casual Fridays across this great country.

Early in his Hawaiian shirt manufacturing career Shaheen got two major endorsements when Frank Sinatra and Elvis Presley agreed to wear his trendy tropical shirts.

Tom Selleck, Magnum P.I. (1980-1988)

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Tom Selleck's "Jungle Bird" shirt, worn by his character, Thomas Magnum, on Magnum P.I., is probably the most popular Hawaiian shirt pattern of all time. During the run of Magnum P.I., the design sparked a Hawaiian shirt resurgence, and to this day, these shirts sell for a pretty penny at auction. Selleck's distinctive shirt has become such an icon that the original is now part of The Smithsonian's American History collection. You can purchase your own replica model at fine retailers everywhere.

Jim Carrey, Ace Ventura: Pet Detective (1994)

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By 1994, the public perception of the Hawaiian shirt had changed. Ace Ventura (Jim Carrey), like Magnum, is a detective, but where Tom Magnum pulled off a slick, cool vibe, Ace was a boisterous, obnoxious loud mouth. By the 90s, the Hawaiian shirt had become a hallmark of the kind of guy who thinks he's the life of the party, the guy prone to dancing on the bar or taking his shirt off unprompted, that guy that maybe next time you'll conveniently "forget" to invite out.

Ace Ventura, a guy full of jokes that only he finds funny and annoys every human he comes in contact with, is the paragon of the 90s Hawaiian shirt wearing dude. In the 90s, wearing a Hawaiian shirt was an easy way to tell the world, "Do not go in there!"

Nicolas Cage, Raising Arizona (1987)

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Nicolas Cage's wardrobe in Raising Arizona is part of a clear transition in the status of the Hawaiian shirt in American culture. What was once a symbol of effortless cool slowly morphed into a calling card for lower class goofballs. There was something cool about Hi McDunnough, but there was a great distance between how cool he actually was and how cool he was in his own mind. The would-be criminal imagined himself as a latterday Babyface Nelson, but in reality, he could barely steal a pack of diapers. Magnum P.I. and Hi McDunnough both drove fast, but Hi tended to crash his car and end up in prison.

Nick Nolte, DUI Arrest (2002)

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Hawaiian shirts are for party animals. That's just a fact. But sometimes, those animals party a little to hard. Such was the case with Nick Nolte in 2002. This photo was from a DUI arrest, but is not actually a mug shot. Nolte told GQ in 2012 that a cop actually asked to take a Polaroid shot of him and Nolte allowed him to as long as he shared the proceeds with his colleagues.

Jimmy Buffet (1971-Present)

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Many modern day musicians owe a huge debt to Jimmy Buffet. Before alt. acoustic rockers like Jack Johnson and easy going country artists like The Zac Brown Band started making obscene amounts of money singing about the beach, Buffet was building his oceanfront empire. Buffet began his music career in the 60's, peddling a version of the day's popular country-folk sound around the South, from Nashville to New Orleans. After Jerry Jeff Walker took him on busking expedition in 1970, Buffet relocated to Key West, where he was inspired to establish his beach bum persona. And the rest is a history littered with promotional opportunities, from restaurants to casinos to beer to children's books.

Throughout his journey from playing street corners to selling out stadiums to minting money with his Margaritaville brand, Buffet has had a Hawaiian shirt on his back.

Al Pacino, Scarface (1983)

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Though the Hawaiian shirt has gone through multiple cycles of cool and uncool, rarely has the Hawaiian shirt been dangerous. One time when a Hawaiian shirt carried an element of violence was in 1983's Scarface. When Tony Montana begins his reign of terror, he wore a red Hawaiian shirt. Smart move on Tony's part, as the blood stains tend to blend in.

It bears mentioning, however, that the Hawaiian shirt only took Tony so far. Once he started dealing coke by the mountain, he switched to white suits and semi-automatic accessories.

Jeff Cohen (Chunk), The Goonies (1985)

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In The Goonies, Chunk proved that you're never too young to be a big galoot. Chunk also proved that the personable style of a galoot can save the day. Chunk befriends Sloth over their mutual love of food, which leads to the Goonies ultimate victory. Perhaps more importantly, he learned that you are never too young to wear a Hawaiian shirt with pride.

Leonardo DiCaprio, Romeo + Juliet (1996)

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It might be a little generous to claim that Leo made it okay to wear a Hawaiian shirt again, but it is fair to say that he was ahead of the curve. The wayward, lovelorn teens of Romeo + Juliet knew that Hawaiian shirts were once dope and could be dope again. Before menswear blogs understood that floral print shirts were actually fly, Leo/Romeo was stunting in the streets of Verona Beach.

Our verdict: we definitely recommend picking up fly shirts like these, but maybe avoid any kind of suicide pact with a lover.

John Hamm, Mad Men (2013)

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On the eve of the great Hawaiian shirt renaissance, Don Draper reminded us of the heyday of the Hawaiian shirt, when Madison Avenue businessmen wore them in a stylish attempt to cut loose. Even someone who broods as much as Don Draper can make room for a few vibrant pieces of wardrobe. If the smoldering, secretive ad man can take a walk on the wild side, there is no reason that you shouldn't have floral prints in your arsenal.

Johnny Depp, Fear and Loathing in Las Vegas (1998)

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Terry Gilliam's trippy attempt at capturing the mind of Hunter S. Thompson on film has become a modern classic, and with good reason. Gilliam and Depp found a way to illuminate Thompson's worldview while creating a product that is uniquely their own. The success of the adaptation was due largely to their respect and reverence for Thompson's work, and their commitment to reproducing his unique outlook on the silver screen. Depp went as far as to use some costume and prop items that actually belonged to Thompson, including hats, a patchwork jacket, a silver medallion, and, of course, his Hawaiian shirts.

John Candy, Various Films (1980s)

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Though Chris Farley and John Goodman give him a run for his money, John Candy may be the biggest galoot in history. His particular brand of endearing, mischievous, and hilarious characters were the kind of man that Hawaiian shirts were made for. These characters would fit right in at any party, no matter who else was invited. You get a sense that they could man any grill at anywhere at any time. During his unparalleled late 80s hot streak that included Uncle Buck, Planes, Trains and Automobiles, and Who's Harry Crumb?, Candy could often be seen sporting his signature Hawaiian print.

John Candy may have been the perfect Hawaiian shirt wearer. May he rest in peace and Aloha print.