American artist Georgia O'Keeffe (1887–1986) created a series of sketches, paintings and photographs based on her more than nine-week visit to four of the Hawaiian Islands in the Territory of Hawaii in the summer of 1939. Her trip was part of an all-expenses-paid commercial art commission from the Philadelphia advertising firm N. W. Ayer & Son on behalf of the Hawaiian Pineapple Company, later known as Dole. The company arranged for O'Keeffe to paint two works, without any artistic restrictions, for a magazine advertising campaign for pineapple juice. Two of the paintings from this commission, Crab's Claw Ginger Hawaii and Pineapple Bud, were used in advertisements that appeared in popular American magazines in 1940. Her photos of Hawaii, all from the island of Maui, are said to be her first major works in that medium up to that point.

The exhibition of O'Keeffe's complete Hawaii series of paintings, comprising tropical flowers, landscapes, and cultural artifacts, has only been shown together in their entirety once, appearing in O'Keeffe's original showing at An American Place from February 1 to March 17, 1940, which was positively received by critics at the time. The original exhibition led to the sale of one work, Cup of Silver Ginger, which contemporaneously entered the collection of the Baltimore Museum of Art. Subsequent public exhibitions in 1990, 2013, and 2018, have shown only part of the series due to six of the paintings in the series being held in disparate public and private collections. In 2021, O'Keeffe's Hawaii photos from the series were first shown in a traveling exhibition dedicated solely to her photography.

Background Georgia O'Keeffe was raised on a large, rural dairy farm in Sun Prairie, Wisconsin, in the late 19th century. Her exposure to nature contributed to her artistic development at a young age. O'Keeffe's mother educated and encouraged her daughters to study art. O'Keeffe studied art at a Catholic girls' high school, where she first focused on larger images in her paintings in response to a nun who criticized a drawing of two hands she had made as tiny and out of proportion. After high school, she took life drawing classes at the School of the Art Institute of Chicago under John Vanderpoel, whose impact would stay with her throughout her life. She left the school after she came down with typhoid, forcing her to recover at home for a time.Wright 1996, pp. 4–7. By 1907, O'Keeffe was well enough to begin studying at the Art Students League in New York with William Merritt Chase, who taught his students to work quickly and to create a new painting each day.

She won a scholarship in 1908, but financial problems caused O'Keeffe to leave art school and move to Chicago in late 1908, where she worked as a commercial artist. She took freelance commercial commissions in the fashion advertisement industry and corporate and business commissions in Chicago and New York, drawing lace and embroidery designs for women's clothing advertisements, often for 12 hours at a time, six days a week.Lisle 1997, pp. 52–53; Wright 1996, pp. 4–7. Her job required illustrators to quickly produce work for daily newspaper deadlines, and there was no end to job opportunities for those who could keep up. It was often rumored that O'Keeffe was the uncredited designer of the logo for Old Dutch Cleanser.Drohojowska-Philp 2005, pp. 72–74, 76; Lisle 1997, p. 53. O'Keeffe later credited Chase for teaching her to paint quickly, a skill that was useful in the fast-paced commercial art world. O'Keeffe was not happy with working in advertising to the exclusion of all else, nor was she fond of the teeming city of Chicago, with its harsh winters and polluted air.Lisle 1997, pp. 52–53.

O'Keeffe came down with the measles in 1910, leaving her vision too weak to continue illustrating advertisements.Lisle 1997, p. 53. This forced her to recover with her family, who were now living in Virginia, putting an end to her commercial pursuits. She stopped painting at this point, realizing her academic study had only taken her so far. O'Keeffe recalled: "I began to realize that a lot of people had done this same kind of painting before I came along. It had been done and I didn't think I could do it any better."Kuh 1962, p. 189. She enrolled in drawing classes at the University of Virginia, Charlottesville, in 1912. Noticing O'Keeffe was no longer painting, her sister Anita invited her to take classes from Alon Bement who was training students to teach art to children. Bement relied on the Dow Method, the artistic approach of his mentor, Arthur Wesley Dow, a mostly unknown artist and arts educator innovator. O'Keeffe attended courses by Dow at Teachers College, Columbia University, in New York in 1914, embracing Dow's philosophy to "produce original work" and "fill a space in a beautiful way".Wright 1996, p. 7; Kuh 1962, p. 189. O'Keeffe taught art at Columbia College in South Carolina in 1915.

At the age of 28, she made the rash decision to destroy all of her existing artwork, concluding it was too derivative. Going in an entirely new direction, O'Keeffe put her color palette aside for several years and worked in black and white, using charcoal to create original abstract expressionist works. Sharing her new style with Anita Pollitzer, O'Keeffe swore her to secrecy. Pollitzer instead shared them with photographer Alfred Stieglitz (1864–1946).Riley 1995, p. 168. Stieglitz showed O'Keeffe's work at his gallery in 1916, giving her an entire show to herself the next year. They soon married in 1924. Stieglitz was opposed to commercial art, and his position created friction between the two of them.Saville 1990, pp. 15–16. O'Keeffe's increasing use of bright and radiant colors attracted attention with her Fifty Recent Paintings exhibition in 1926. O'Keeffe was approached by Edward Bernays on behalf of the Cheney Brothers Silk Manufacturing Company, commissioning her to create five paintings of flowers paired with silk women's clothing styles. Her paintings were reproduced as posters and window displays to promote Cheney Brothers fashion in retail stores.Blaszczyk 2006, pp. 228–246; Scott 2020, pp. 29–33.

Ayer commission By the late 1930s, O'Keeffe was highly productive and sought after, and her profile as an artist had reached a crescendo with multiple exhibitions and mixed, yet positive reviews. In April 1936, she and Stieglitz moved into the Arno penthouse at 405 East Fifty-fourth Street. Months later, Elizabeth Arden, then one of the wealthiest women in the world, commissioned O'Keeffe to paint Jimson Weed (1936) for her Gymnasium Moderne, a New York salon and fitness center. In 1937, Steuben Glass Works invited 27 artists, including O'Keeffe, Henri Matisse, Isamu Noguchi, and Salvador Dalí, to design crystal works for the company. O'Keeffe took the commission, designing a jimsonweed flower which was etched on a crystal bowl.Robinson 1999, p. 427.

By February 1938, Life magazine was calling O'Keeffe "America's most famous and successful woman artist". In May of that same year, she received an honorary doctorate from the College of William & Mary, which was arranged by Earl B. Thomas, an old friend of O'Keeffe's who was now working for Philadelphia advertising firm N. W. Ayer & Son as an executive.Drohojowska-Philp 2005, pp. 363–376. Ayer was commissioning famous artists for their clients, bringing fine art to commercial advertisements. Ayer represented the Hawaiian Pineapple Company account, and Thomas would soon make O'Keeffe an offer to join their campaign. By July, O'Keeffe told friend and fellow artist William Einstein that she was considering taking the commission.Cowart et al. 1987, pp. 224–226; Saville 1990, pp. 11–12.

In the 1930s, Ayer art director Charles T. Coiner was partly responsible for the popularity of marketing fine art with commercial products, particularly for clients like DeBeers, Steinway & Sons, and the Container Corporation of America. Coiner hired modern artists to persuade customers of the quality of purchasing products made by Ayer's clients in high-end magazine advertisements.Saville 1990, pp. 11–13. In 1932, Hawaiian Pineapple (later known as Dole) had come close to bankruptcy during the Great Depression. To get out of the red, they spent $1.5 million on advertising, using famous artists to generate interest in their product.Bogart 1995, pp. 157–170.

Coiner took the Dole account in 1933, making changes to their advertising strategy. Before coming to Ayer, Dole focused on the health and nutrition of pineapple. Coiner turned this around and changed the product attention to Hawaii itself. Japanese-American painter Yasuo Kuniyoshi and California Scene painter Millard Sheets were matched with Hawaiian Pineapple Company advertisements. Coiner next invited American artist Isamu Noguchi and modernist painter Georgia O'Keeffe to join the campaign. In the summer of 1938, O'Keeffe was offered an all-expenses paid, nine-week trip to the territory of Hawaii as a commercial art commission for the Hawaiian Pineapple Company. In exchange, O'Keeffe agreed to produce two paintings without artistic restrictions for a magazine advertising campaign for canned pineapple juice. O'Keeffe was hesitant at first, but Coiner managed to convince her to take the commission.Saville 1990, pp. 11–13; Bogart 1995, p. 162.

Voyage to Hawaii

Before traveling to the Territory of Hawaii, O'Keeffe's knowledge of the islands came mostly from travel brochures designed for tourists, preconceived ideas that O'Keeffe would have to master to create an original artistic approach and vision about Hawaii in her work.Papanikolas 2013, p. 11. By late January 1939, O'Keeffe finished hanging her annual exhibition of paintings at An American Place, Stieglitz's largest gallery. The showing, Georgia O'Keeffe: Exhibition of Oils and Pastels, ran from January 22 to March 17. It featured 22 paintings in her absence, as she departed for Hawaii a week after the exhibition opened.Drohojowska-Philp 2005, pp. 379–380; O'Keeffe 1939, n.p. She left for the Hawaii Territory on January 30 from Grand Central Station in Manhattan.Saville 2011, pp. 7–8. After arriving in San Francisco, O'Keeffe boarded the SS Lurline, a Matson luxury cruise ship, on February 3.Scott 2020, pp. 29–33. The ship took her to Oahu, arriving in Honolulu on February 8.Saville 1990, p. 13. The entire trip, from New York to Hawaii, took her nine days.

Arrival, interisland travel O'Keeffe's ship arrived at Honolulu Harbor on February 8, 1939. She was met by a representative from Ayer (thought to be John S. Coonley) who took a tender out to the boat. Helen Richards, the wife of Atherton Richards, president and manager of Hawaiian Pineapple, waited for O'Keeffe on the dock. Both Coonley and Richards brought O'Keeffe traditional flower leis as a greeting, which greatly impressed her. After her arrival, O'Keeffe checked into the Moana Hotel in Waikīkī as a guest. In a radio postal telegraph to Stieglitz soon after, she writes: "Arrived this morning feeling fine. Lovely summer weather here. Hope you are alright."Saville 2012, pp. 88–91, 123.