This collection is made up of personal letters related to the immediate and extended family of Philip Mason Sears, including his wife, Zilla MacDougall; his children, Charlotte and Philip Sears; Zilla's sister, Charlotte MacDougall; and Zilla's brother-in-law, Danish diplomat Henrik Kauffmann.
Much of the early correspondence revolves around Zilla MacDougall Sears, including letters that she wrote to her parents, grandparents, and sister about her foreign travels and life in the United States in the 1910s and 1920s. She visited London, England, in 1916 and 1917, and went to Copenhagen, Denmark, and Berlin, Germany, in the early and mid-1920s. In 1925, she described her travels in China, particularly her experiences in Peking (Beijing). Zilla also discussed her life in Syracuse, New York, and family life in Dedham, Massachusetts, after her marriage to Philip Mason Sears in 1924. In December 1924, the couple received congratulatory telegrams. The collection also contains many telegrams from the 1920s and 1930s concerning family health and family travels, including items sent by William MacDougall and Philip Mason Sears.
Additional early items include letters that Henrik Kauffmann wrote to Philip Mason Sears in the 1910s and 1920s, and letters that Charlotte MacDougall Kauffmann wrote to her parents and sister in the 1920s. Henrik and Charlotte's correspondence, often written on Danish stationery, concerns their travels and lives in China, India, Thailand, Japan, Denmark, and other locations. Prior to their marriage, Henrik discussed his excitement about Charlotte's upcoming visits and otherwise commented on their relationship. Correspondence from the 1930s includes additional travel letters and telegrams, and a group of letters to Zilla MacDougall Sears regarding her desire to purchase a Sicilian donkey from a company in Palermo in 1933. Zilla also wrote a letter to her mother on "swastika" stationery from Cuernavaca, Mexico (March 7, 1936).
Much of the material from the World War II era concerns the naval service of Philip Mason Sears and Philip Sears, Junior. The Sears children wrote a small number of V-mail letters to their father while he was stationed on the USS Fuller in the Pacific in 1942. From 1944 to 1946, Philip Mason Sears, Jr., wrote to his parents and sister about his experiences in the navy, including his participation in the V-12 Navy College Training Program at Dartmouth College in Hanover, New Hampshire, and his later experiences on a base in the Nevada desert. He often discussed his desire and attempts to gain entry into the aviation service and/or gunnery school. Additional correspondence from the early to mid-1940s includes letters that Charlotte Sears ("Poppin") wrote to her family about her studies and other experiences at the Foxcroft School in Middleburg, Virginia. Many of her letters feature cartoonish doodles and drawings. Zilla MacDougall Sears also received letters her nieces and nephews, including David and "Liza Jane" (who included colored drawings of horses in her letter postmarked from Lake Placid, New York, on July 18, 1942). The Sears children also received letters from their aunt, Charlotte MacDougall Kauffmann, then living in Washington, D.C.
After the war, the bulk of the collection is comprised of letters from Henrik and Charlotte MacDougall Kauffmann and Charlotte Sears (later Look) to Zilla MacDougall Sears. The Kauffmanns wrote to Zilla after returning to Denmark in 1946; among other topics, they discussed some of the lingering effects of the war. In the early 1950s, Charlotte Sears and her husband, David T. Look, wrote to Zilla about their experiences in Washington, D.C., including their work and leisure activities. In 1953, Charlotte described her travels in southern California and in Europe. The final items largely consist of Charlotte Kauffmann's letters to Zilla Sears from Switzerland and Denmark as late as 1963; while in Switzerland, she mentioned her participation in winter sports.
Additional materials include newspaper clippings about the death of Clinton MacDougall and the atomic bomb, the Sears children's school essays, and other miscellaneous manuscripts. A small number of picture postcards are present throughout the correspondence. The collection's photographs and negatives pertain to United States sailors and to people at leisure indoors and outdoors.