On a yellow diamond-shaped insignia, the upper half arched and edged with a 1/8 inch (.32 cm) red border, a yellow horse and rider outlined and detailed red below the inscription "ROOSEVELT HIGH SCHOOL" arching at top in red letters. The overall dimensions are 3 1/2 inches (8.89 cm) in height by 3 inches (7.62 cm) in width.
Red and yellow are the school colors are well as the traditional colors associated with the Hawaiian monarchy; they reflect the school's heritage. The mounted rider symbolizes a Rough Rider, the school's mascot, and alludes to the school's namesake.
The shoulder sleeve insignia was originally authorized 29 June 1950. It was cancelled due to a new design and updated description and symbolism on 26 April 1994. (TIOH Drawing Number A-10J-337)