Colorful? Yes. Comfortable? For sure. Tacky? Depends on who you ask. Hawaiian—or “Aloha”—shirts are among the world’s most polarizing garments. Their vibrant journey to the mainland and beyond is a tale of surfers, sailors, and cultural crossroads.

Tropical Ancestry

Though Hawaii was still self-governed during the 1880s, U.S.-run businesses dominated the local economy. Seeking cheap labor, American plantation owners enlisted workers from elsewhere. Chinese, Korean, Portuguese, and, in the largest numbers, Japanese immigrants came pouring over.

Fittingly, Aloha shirts have Japanese roots. Those who’d left their homeland often brought with them bright kimono fabrics. Meanwhile, Filipino and Chinese newcomers brought barong talongs (a traditional type of untucked shirt) and multicolored silks, respectively.

On top of those foreign influences, Hawaiian shirts were also inspired by native fashions. Before the 1800s, most Hawaiians created clothes with tapa (or “kapa”) cloth. Made from tree fibers, the material was colored with red and yellow vegetable dyes, which tended to fade fast.

When the age of plantations arose, new fabrics caught on. Working in the fields required tough, heavy, and reasonably cheap clothing. Enter the palaka. Named after the Hawaiian word for “frock,” these checkered, denim items were perfect for outdoor drudgery. However, unlike true Alohas, they mostly had long sleeves.

Creation and Early Rise

Historians agree that the first bona fide Hawaiian shirts emerged in the 1920s. Though we don’t know who originally came up with the concept, some founding fathers deserve shout-outs.

In the '20s, University of Hawaii student Gordon Young worked with his mother’s dressmaker to develop a “pre-aloha shirt.” For fabric, they chose Japanese yukata cloth, which is usually used in light robe construction. Patterns included bamboo and geometric shapes over white backgrounds. Soon enough, his classmates started rocking similar tops. Young would later attend the University of Washington, where this revolutionary fashion statement turned plenty of heads.

Aloha shirts also owe a tremendous debt—and their very name—to Chinese-Hawaiian businessman Ellery Chun. After graduating from Yale with a degree in economics, Chun returned to his family’s dry good store in Honolulu in 1931. With the Great Depression in full swing, Chun’s establishment—like thousands of others—looked destined for collapse.

Then, in 1936, a light bulb went off. As he told the Honolulu Star-Bulletin many decades later, “I got the idea to promote a local style of shirt.” Like Young, he chose yukata cloth, and Chun's sister Ethel created tropical designs. Their finished products were placed “in the front window of the store with a sign that said ‘Aloha Shirts.’” (Being business-savvy, he copyrighted the term.) “They were a novelty item at first,” says Chun, “but I could see that they had great potential.” He wasn’t wrong.

Shortly thereafter, Hawaiian shirts underwent mass production. On the front lines stood Alfred Shaheen, a WWII veteran who’d set up his own clothing business (“Shaheen’s of Honolulu”) in 1948. Alohas were his big specialty, and as sales boomed, he hired a team of local artists to design lively motifs that included Japanese, Chinese, and Hawaiian imagery. By 1959, Shaheen had 400 employees and netted over $4 million in annual profits, making him the new state’s foremost Aloha shirt manufacturer.

A hit with beach-goers, the product also presented off-duty naval servicemen with a striking alternative to their drab uniforms. Upon returning home, recruits would bring along their new souvenirs. Coupled with the dawn of commercial airline flights to Hawaii, this drove sales through the roof. As one marketing campaign put it, they were effectively “wearable postcards.”

Hollywood star power added yet another boost. Montgomery Clift and Frank Sinatra famously donned Alohas in 1953’s From Here to Eternity. Bob Hope sported several throughout his The Road film series. And Elvis Presley stunned fans in a bright red one on the cover of the Blue Hawaii soundtrack in 1961.

Of course, the fact that several Presidents (such as Harry Truman and Richard Nixon) have been pictured wearing them didn’t hurt, either. However, Hawaii native Barack Obama drew a line in the sand and publicly declined to sport an Aloha shirt at the 2011 Asia Pacific Economic Cooperation forum (APEC) held in Honolulu. Traditionally, world leaders are expected to pose for a group photo while wearing some article of clothing that represented the host nation. This time, however, America’s commander-in-chief made compliance optional.

“Two years ago, when I was in Singapore and it was announced that we would be hosting the APEC Summit here in Honolulu, I promised that you would all have to wear aloha shirts or grass skirts," Obama reminded his colleagues. "But I was persuaded by our team to perhaps break tradition, and so we have not required you to wear your Aloha shirts, although I understand that a few of you have tried them on for size, and we may yet see you in them in the next several days."

Ultimately, no one put theirs on come picture time.

“Aloha Fridays”

If your workplace relaxes its dress code once a week, go ahead and thank tropical garb devotees. Hawaii can get unrelentingly humid, which isn’t the best environment for dark, heavy business suits. The '60s saw Honolulu’s fashion industry launch “Operation Liberation,” a campaign designed to promote the wearing of lighter, more informal duds around Hawaiian offices.

Aloha shirts were the movement’s centerpiece—proponents even gave two free ones to every single member of the State Senate and House of Representatives. Their efforts paid off and over the summer of ’66, government employees were encouraged to wear Hawaii shirts on Fridays. Once that custom—dubbed “Aloha Fridays”—reached America’s lower forty-eight, it adopted a new name. Today, we call it “Casual Friday.”