An Indian head, resembling the Milwaukee Braves logo at the time,[1] represents Native American origins.

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, with the 1846 date of city incorporation from the merger with Byron Kilbourn's Kilbourntown and Solomon Juneau's Juneautown on the flag's right vertically.

The winning entry, designed by John Amberg, included an oak branch with the motto "Steady Progress" over a cream-colored field.

[13] In 1927, a group of citizens created their own flag, a field of Alice blue with the city seal in golden orange in the center.

In 1942, Alderman Fred P. Meyers introduced a new resolution in the Common Council proposing "a special city flag committee composed of aldermen and public-spirited citizens who, with the co-operation of the art commission and other art institutions would be commissioned to recommend a design to be ready for Milwaukee's one hundred birthday" on January 31, 1946.

The winner was 17-year old Milwaukeean Alfred P. Dannenmann, who created a flag featuring three interlocking gears labeled "HOMES", "INDUSTRY", and "SHIPPING" between a banner reading "MILWAUKEE" and the date "1846".

Instead, the city's art commission decided to design a new flag itself, incorporating elements of several entries from the previous year's contest.

[18] The city intends to preserve the painting and digitize it, in part to correct the inaccurate version found on Wikipedia.

Lee Tishler, a Milwaukee Public Museum employee, won with a bright yellow swallowtail banner featuring bold symbols of civic life: people, parks, industry and lakefront.

Although Tishler was awarded the contest's prize of a $100 savings bond in a ceremony at City Hall, his flag was not adopted.

[22] In a 2004 poll conducted by the North American Vexillological Association, the flag of Milwaukee was rated the fourth worst of all major cities in the United States.

[31] In November of that year, the City of Milwaukee's Arts Board said the original search for a new flag was not inclusive enough, with the relatively small number of judges and voters involved in the process.

[34][35] The organizers of the contest released the design into the public domain, deciding to let the flag gain popular acceptance before pushing for official recognition.

Since its introduction, the People's Flag has been adopted by local businesses and used on commercial products from bicycles to microbrew labels.

[37] This commercial availability, and the demand driving it, has led the People's Flag to become "a near-ubiquitous symbol across town", even without being officially adopted by the city government.

Bauman's suggestion inspired a series of humorous posts online, with commenters slapping all manner of "local symbols" (including sports figures, convenience stores, and a prominent Milwaukee attorney) to the People's Flag.

Bauman was able to delay the vote on adopting "Sunrise Over the Lake" on a procedural matter over the estimated $917 it would take to replace the city's twenty physical copies of the official flag.