On a shield shaped embroidered item edged with a 1/8 inches (0.32 cm) blue border, blazoned as follows: Argent (Silver Gray), a stylized rider Or, upon a horse Argent, detailed Azure, to sinister. Attached above the item a silver gray scroll edged with a 1/8 inch (0.32 cm) blue border inscribed ROOSEVELT in blue. The overall dimensions are 3 1/4 inches (8.26 cm) in height by 3inches (7.62 cm) in width.

Blue and gold are the school colors. The rider upon horseback alludes to President Theodore Roosevelt, from his time leading the Rough Riders during the Spanish-American War. The school is named for the 26th President; chosen for his bold personality and natural leadership qualities.

The shoulder sleeve insignia was authorized 26 October 2018. (TIOH Drawing Number A-10J-1236)

On a shield shaped gold metal and epoxied device 1 1/8 inches (2.86 cm) in height blazoned as follows: Quarterly Or and Sable, a sword bendwise of the second, point to chief and throughout, between in the second quarter a stylized rider upon a horse in full gallop and in the third quarter, a torch enflamed of the first; the shield is surmounting a laurel wreath Vert. Attached below the shield and wreath, a blue scroll bearing the inscription ROOSEVELT U.F.S.D (Union Free School District) in gold.

Blue and gold are the school colors. The torch is emblematic of knowledge and education. The sword signifies leadership and a military foundation. The rider upon horseback portrays President Roosevelt, for whom   the school is named. Black and gold are associated with the Army and the ROTC program.

The shoulder loop insignia was authorized 26 October 2018.