-Frances Clara Cleveland Preston (née Folsom, christened Frank Clara; July 21, 1864 – October 29, 1947) was the first lady of the United States from 1886 to 1889 and again from 1893 until 1897, as the wife of President Grover Cleveland. She was the first and (as of 2024) only person to serve in this role during two non-consecutive terms.

Cleveland became involved in education advocacy, serving on the Wells College board, supporting women's education, and organizing the construction of kindergartens. Grover Cleveland died in 1908 and in 1913, Frances married Thomas J. Preston Jr.. She continued to work in education activism after leaving the White House, becoming involved with Princeton University. During World War I, she advocated military preparedness.

Cleveland maintained an openness with the public that was not shared by her husband or by her predecessor Rose Cleveland. To accommodate all who wished to visit the White House, she hosted many social events on Saturdays to ensure that they did not conflict with the schedules of working women.  Cleveland received countless letters from the American people, many of them asking her to influence the president's granting of patronage jobs. She read all of the mail that she received, but she sought assistance from the president's secretaries in replying, eventually hiring her friend Minnie Alexander as a personal secretary.  Her openness extended to the White House staff as well, with whom she maintained close relationships.

-Rose Elizabeth "Libby" Cleveland (June 13, 1846 – November 22, 1918) was an American author and lecturer. She was acting first lady of the United States from 1885 to 1886, during the presidency of her brother, Grover Cleveland. Receiving an advanced education in her youth, Cleveland rejected traditional gender norms and sought a career for herself in a variety of literary and academic positions. When her unmarried brother was elected president, she acted in the role of first lady until his wedding with Frances Folsom. She used the role of first lady as a platform for her support of women's suffrage, expressing little interest in the household management associated with first ladies.

After leaving the White House, Cleveland authored several fiction and nonfiction works, many relating to women's rights.

Cleveland held strong progressive opinions, and she continued to express them while she was acting as first lady. She publicly supported women's suffrage, and she supported the temperance movement, banning wine in the White House. She lived by the ideal of the New Woman that was advocated by the feminist movement of the time. She was sympathetic to the Victorian dress reform movement, but she limited herself to wearing low-cut dresses that exposed her shoulders—still a controversial choice. Cleveland used her platform as first lady to promote the Women's Anthropological Society, which advocated the inclusion of women in science. She still held other prejudices common of the time, advising her brother not to appoint a significant number of Catholics to government positions.

After reuniting, they moved to Italy in 1910, where Cleveland spent her final years engaged in relief efforts for war refugees during World War I and then for Spanish flu patients before contracting the disease herself and dying in 1918.