The Robert L. Simons Collection is comprised of materials relating to Simons’ career as a military and commercial pilot from the 1920s-1940s, including logbooks, military records, photographs, and films.

There are six logbooks from Simons’ time as a commercial pilot in various U.S. cities spanning from 1928-1947. Several licenses and cards are included, include pilot's and mechanic's licenses, a radio operator's license, a military identification card, and membership cards for the OX5 Aviation Pioneers and Veterans of Foreign Wars. The collection's photographs are comprised of several portraits of Simons, some in his U.S. Army Air Forces uniform, and a portrait of an unidentified man. There is also a folder of assorted clippings.

The films, which were likely taken by Simons, contain a mix of content, such as travel and aerial footage, National Air Race footage, and footage depicting commercial and U.S. military aircraft. The films are from the late 1930s and early 1940s. They range from under a minute to 17 minutes in length. Because Simons most likely shot the footage, he does not appear in any of the films.

The collection also includes short snorter bills consisting of signed bank notes from Algeria, Egypt, the Republic of China, Morocco, Greenland, Mexico, Canada, and the United States.