"The official flag of Milwaukee was adopted in 1955. It is a medium blue, displaying various symbols of Milwaukee. The center industry gear bears symbols of Milwaukee's history: an Indian head representing Native American origins, a church steeple, and a tiny version of Milwaukee's Civil War flag. Below this is Milwaukee City Hall, representing good government, which is flanked by a church, a factory, and the now-demolished County Stadium. The golden barley stalk on the left represents Milwaukee's brewing history, and the red ship with water symbolizes Milwaukee's status as a port city. Milwaukee was incorporated in 1846.
Buildings - Flags
In the 1950s, Milwaukee leaders discovered it was one of only four cities with a population over 500,000 without a flag, and so held a contest for flag designs. Former alderman Fred Steffan combined elements of some of the better entries to create the current flag.
In 2001, the Milwaukee Arts Board of the Milwaukee Common Council held a contest to attract designs for a new flag. Over 105 designs were submitted, but none met with the approval of the board, and the old design was kept. According to the North American Vexillological Association, Milwaukee's flag is one of the 5 worst in the nation."