It was In South Carolina that she began to experiment with charcoal. She sent a series of abstract charcoal drawings to a classmate from Columbia, Anne Pollitzer. .
Anne, going against Georgia's wishes to not show the drawings to anyone brought them to Alfred Stieglitz. "They are the purest, finest, sincerest things to enter 291 in a long while," he said. He exhibited ten of her drawings.
In the fall of 1916 Okeefe took a job teaching at West Texas State Normal College. During this time she would take trips to the nearby Paolo Duro, hiking down the step slopes to observe the rich vibrant colors of the canyon. She abandoned charcoal at this point and while in Texas painted at least fifty watercolors. Stieglitz exhibited them in Okeefe's first solo show at 291 in April of 1917. .
During that winter Okeefe came down with a flu that was sweeping the country. She was force to take a leave of absence from her teaching and eventually resign. It is possible that pressures form the community due to Okeefe's radical views about US involvement in WW2 added to her decision to leave. .
Stieglitz encouraged Okeefe to return to New York. He was at the end of a failing marriage and wished to pursue a relationship with Georgia. When she arrived in New York they moved into his studio, he being fifty-four, she being thirty-one. Stieglitz besides owning 291 was a photographer and an art critic. He pioneered the art of photography and introduced America to the art of Picasso, Matisse, and Cezanne. Besides being Okeefe's most avid supporter, organizing her shows and selling her paintings, Stieglitz took more than three hundred portraits of her between 1918 and 1937. He exhibited a portion of them, a series of her face and body photographed nude, at his gallery in 1921. It caused quite a sensation. .
It was during these long New York winters that Georgia began to paint her huge flowers, some of her most popular and famous works today.