Hawaii's flag should not, by the usual logic of flags, exist in its current form. It puts the British Union Jack on an American state flag, over stripes that nod to the American ensign, in an arrangement designed for a Pacific kingdom trying to stay on good terms with two empires at once. It worked. The same eight stripes and canton have flown over a kingdom, a republic, a territory, and a state, and in the 2001 North American Vexillological Association survey it ranked 11th of 72, in the top sixth of the field.
A gift from Vancouver
The story starts with George Vancouver, the British navigator who had sailed with Cook and returned to the islands three times between 1792 and 1794. In February 1794, anchored at Kealakekua Bay, Vancouver concluded an agreement with Kamehameha I, the chief then in the process of conquering and uniting the islands, and a British flag was taken ashore and raised. Whether it was a Union Jack or a Red Ensign is debated by historians; either way, the British flag became Kamehameha's flag, and it flew over his growing kingdom for the next two decades.
That arrangement had a shelf life. As American merchant ships came to dominate the sandalwood trade and Honolulu's harbor filled with vessels from Boston, a purely British flag over an independent kingdom became awkward. One often-told story holds that during the War of 1812, Kamehameha was advised that flying the Union Jack could read as taking Britain's side, while flying the Stars and Stripes would offend the British. The tale is unverified, but it captures the real diplomatic problem the new flag solved.
A flag between empires
Around 1816, when Kamehameha bought a Western ship and put the Scottish captain Alexander Adams in command, a distinct Hawaiian flag appeared: the Union Jack kept in the canton, with horizontal stripes filling the field. Adams is often credited with the design, sometimes alongside other advisers, but no contemporary record names a designer. By 1817 the flag had been carried to Canton on a Hawaiian trading voyage, its first appearance abroad.
The early flag was remarkably unstandardized. The Russian navigator Vasily Golovnin, calling at the islands in 1818, recorded seven stripes; other visitors counted nine. The order of colors varied too. What every version shared was the essential idea: British canton, American-style stripes, a small kingdom signaling to both powers that it belonged to neither.
The Paulet affair
The flag's worst year was 1843. In February, Lord George Paulet, a Royal Navy captain acting far beyond his instructions, sailed the frigate Carysfort into Honolulu and forced Kamehameha III to cede the islands to Britain under threat of bombardment. For five months Paulet ran Hawaii, and among his acts was ordering Hawaiian flags destroyed. London wanted none of it. Rear Admiral Richard Thomas arrived in July, repudiated the seizure, and on July 31, 1843 restored the kingdom's sovereignty in a ceremony at what is now Thomas Square in Honolulu, where the Hawaiian flag was raised again. Kamehameha III's declaration that day, "Ua mau ke ea o ka aina i ka pono" (the life of the land is perpetuated in righteousness), became the state motto.
The restoration prompted a cleanup of the flag itself. The number of stripes was fixed at eight, one per major island, and the standardized flag was officially unfurled on May 25, 1845, at the opening of the kingdom's legislature. That is the flag, stripe for stripe, that flies today: white, red, blue from the top, repeated, with the Union Jack in the canton.
One flag, four governments
What happened to Hawaii's government after 1845 is a catalog of upheaval; what happened to its flag is nothing. American businessmen and their allies overthrew Queen Liliuokalani in 1893, and the short-lived provisional government and Republic of Hawaii kept the flag. The United States annexed the islands in 1898, and the Territory of Hawaii kept it. Statehood came on August 21, 1959, and the fiftieth state kept it again, the design passing into the Hawaii Revised Statutes essentially as the kingdom had left it. The statutes fix the proportions (the flag twice as long as it is high, the canton half the hoist) but not the shades of red and blue, so manufacturers typically borrow the colors of the British or American flags.
That continuity gives the flag a double life no other US state flag has. For the state, it is simply the flag. For the Hawaiian sovereignty movement, it is the flag of the kingdom that was overthrown, and flying it upside down, the traditional signal of distress, has been the movement's principal emblem since the 1990s. The state itself acknowledges the layered history: in 1990 Governor John Waihee proclaimed July 31 as Ka La Hae Hawaii, Hawaiian Flag Day, deliberately setting it on the anniversary of Admiral Thomas restoring the kingdom's flag in 1843. The same piece of cloth carries both stories, which is perhaps the most Hawaiian thing about it.
References
[1] Hawaii Revised Statutes § 5-19 (description of the Hawaiian flag). https://www.capitol.hawaii.gov/hrscurrent/Vol01_Ch0001-0042F/HRS0005/HRS_0005-0019.htm
[2] Office of the Lieutenant Governor of Hawaii, "History of the Hawaii Flag." https://ltgov.hawaii.gov/virtual-tour-history-of-the-hawai%CA%BBi-flag/
[3] "Flag of Hawaii," Wikipedia. https://en.wikipedia.org/wiki/Flag_of_Hawaii
[4] Whitney Smith, "Flag of Hawaii," Encyclopaedia Britannica. https://www.britannica.com/topic/flag-of-Hawaii
[5] North American Vexillological Association, "2001 State and Provincial Flag Survey." https://nava.org/digital-library/design/surveys/
[6] Ralph S. Kuykendall, The Hawaiian Kingdom, Volume 1: 1778-1854 (University of Hawaii Press, 1938), on the Vancouver agreement and the Paulet affair.