In the Zalman Schachter collection, housed in the University of Colorado (Boulder, CO) there is a painting of the Rebbe with a Shtreimel, drawn by renowned Chassidic artist R’ Hendel Lieberman.
When the Rebbe was shown this drawing, he asked R’ Hendel: “Why did you draw this?”
R’ Hendel answered: “Because I want to see the Rebbe with a Shtreimel…”
Rumor has it that R’ Hendel also drew an additional painting of the Rebbe in a Shtreimel during a Farbrengen with the Eltere Chasidim, and a crowd around him.
Based on an blogpost by Hirshel Tzig