Bertram K. and Nina Fletcher Little purchased "Gentleman Wearing a Striped Waistcoat" and "Woman Wearing a Bonnet with Pink Ribbons" from the Childs Gallery in Boston in 1966. They were originally found in Brattleboro, Vermont, but no information about the sitters accompanied them. The J. Whatman paper on which the gentleman and woman were painted bear watermarks dating 1825 and 1828, respectively. The pictures are part of an early, atypical group that long challenged attribution to the Shutes because of the stylistic disparities. However, they are linked to the work of the Shutes by a number of striking similarities.

Chronological and written clues that unite this group with work considered typical of the Shutes begin with the letter held by Mary Ann Russell in her portrait which contains a handwritten postmark dated November 4, 1828. The first dated and signed paintings do not appear until 1832, with a pair of portraits of sisters Eliza Parker Townsend and Emeline Parker. Each is signed “Drawn by R.W. Shute and painted by S.A Shute Lowell, Massachusetts,” and they are dated February 17 and 18, respectively. This inscription allowed a number of large watercolor portraits displaying the diagonally striped backgrounds and other unique characteristics of the Parker paintings to be attributed to the two artists named Shute. In 1978 research finally established the identity of the artists. Additional examples of their jointly signed work continued to surface, as well as unsigned paintings that expanded the earlier stylistic parameters, including portraits that were closely related to this superb pair.

The distinctive qualities of the group to which this pair of portraits belongs led to the hypothesis that they might represent the work of Samuel Shute alone, a point of view that was put forth in early Shute research. Since then, many more pictures have emerged, including several key exampled that blur the stylistic boundaries and suggest transitions between artistic approaches that had previously seemed almost unconnected. These revelations brought into question the conclusion that portraits such as this pair were painted solely by Samuel. Ongoing research has extended the timeline of Ruth’s artistic activity thirty-eight years after the death of her first husband. Emerging clues remain to be deciphered, but at this point it seems probably that Ruth was involved in the entire body of work and that she was the dominant creative force in all their collaborative efforts.

Helen Kellogg and Steven Kellogg, "Gentleman Wearing a Striped Waistcoat" and "Woman Wearing a Bonnet with Pink Ribbons," in Stacy C. Hollander, American Radiance: The Ralph Esmerian Gift to the American Folk Art Museum (New York: Harry N. Abrams in association with American Folk Art Museum, 2001), 390–391.