Five By Design had its origins at the University of Wisconsin—Eau Claire as a vocal quartet in 1982. In 1990, the group grew into a vocal quintet specializing in the big band vocals of the 1940-50s, and established itself as a legal entity. In 1994, the vocal group booked its first orchestra engagement with the Milwaukee Symphony.

In 1998, the ensemble included the vocals of Lorie Carpenter-Niska, Kurt Niska, Terrence Niska, Michael Swedberg, and Catherine Farr-Scott. Sheridan Zuther came on board while Farr-Scott took a leave.. Five By Design went on to perform with numerous Canadian orchestras, the Boston Pops holiday tour, the National Symphony at the Kennedy Center and with big bands. After 29 years of international touring, its members moved on and Five By Design closed its doors.