On a Yellow vertical elongated trapezoidal shaped embroidered item, reduced in size at the top, edged with a 1/8 inch (.32cm) blue border, a stylized red sun above a red bricked roadway issuing from base and in perspective, overall and at center a yellow demi-tiger springing towards the front, with white claws, fangs/teeth, and facial features, red tongue and area of mouth, detailed and outlined blue; above the item a yellow scroll inscribed "CHIPLEY" and below the item a yellow scroll inscribed “HIGH SCHOOL” all in blue letters. Overall dimensions are 3 ½ inches (8.89cm) in height by 2  inches (5.08cm) width at the top by 2 5/8 inches (6.67cm) width at base. 

Blue and gold are the colors associated with Chipley High School. Blue denotes cadets’ loyalty to the school and community. Gold symbolizes the students’ bountiful determination for education and military preparation. Red signifies endurance. The brick road alludes to the school location on Brickyard Road in Chipley, Florida. 

The shoulder sleeve insignia was authorized 12 May 2022.

A gold color metal and epoxied circular device consisting of two black front train cars, horizontally placed and back-to-back, above blue railroad tracks issuing from base and in perspective, overall a white stylized tiger’s head, with red pupil of eyes and mouth area, with a black portion in its mouth, garnished gold and detailed blue, above all, a small gold demi-sun, all within a blue circular designation band, inscribed above “CHIPLEY HIGH SCHOOL" and below “TIGERS” all in Gold letters. Overall diameter is 1 1/8 inch (2.86cm). 

Blue and gold are the colors associated with Chipley High School. The trains displayed back-to-back, in opposing directions and placed above the railroad tracks, commemorate William Dudley Chipley. Chipley was the Florida state senator from 1895 to 1897 as well as the president of the Pensacola and Atlantic Railway system, for which the city is named. The sun alludes to the state of Florida and its official nickname as the Sunshine State. The tiger is the school mascot.

The shoulder loop insignia was authorized 12 May 2022.