It is one of the few American city flags to currently feature different designs on the obverse and reverse.

The initial design of the flag was created in October 1899, though the idea was first proposed in April of that year.

After modifications to the design were made, it was readopted as the city flag of Raleigh on April 25 of that year and has remained since.

[2] The red-white-red triband is a reference to the namesake of the city, Walter Raleigh,[1] as red and white were the colors of his arms.

[4] Underneath the tree is text reading "ESTABLISHED 1792",[1] the year land in Wake County was purchased for a planned capital.

Within the ring are two pieces of text: "CITY OF RALEIGH" is on top and "NORTH CAROLINA" is on bottom.

[1] In heraldry terms, Sir Walter's arms would be described as gules, five lozenges in bend, argent.

Below the shield is a red ribbon that reads "Amore et Virtute" (English: "By Love and Valor"), Sir Walter's motto.

[7] In addition, the committee decided that a triband using these colors should be on the flag and also recommended that one side of the flag have an oak tree surrounded by a gold ring with the text "City of Raleigh 1792" and have oak leaves and acorns surrounding the ring.

Denson was not done sewing the flag when the ship made a stop in Wilmington, North Carolina on May 5, 1899.

[9] Denson finished the flag in October of that year, and it soon flew at the North Carolina State Fair.

On one, a red-white-red vertical triband featuring the recommended oak tree in a gold ring with the leaves and acorns, differing from the committee's suggestion by using the text "City of Raleigh, North Carolina" (not just City of Raleigh) in the top half and "1792" in the bottom half.

[13] The flag also received local news coverage when the city council considered redesigning it in 2015.