She received her MFA from Massachusetts College of Art in 1980. Olin has shown in exhibitions across the U.S., Canada, France, Poland, Serbia, South Africa, and Cuba. Her work is in the permanent collections of the Boston Public Library, Temple Israel, Brookline, MA, YIVO Institute, NYC, The DeCordova Museum, Lincoln, MA and the Fogg Art Museum, Harvard University. In 2004 Debra was awarded the Rappaport Prize, the largest public annual award to an individual artist in New England. In 2018 Olin received a Massachusetts Cultural Council Finalist Award and a grant from the Berkshire Taconic Artist Resource Trust.