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The Surprising Military Origins of Letterman Jackets Before letterman jackets became a symbol of high school pride, they were actually born on the battlefield. Here’s a little-known fact: The classic wool-and-leather design we know today was inspired by 19th-century military uniforms specifically, the heavy wool coats worn by cavalry soldiers.... The Surprising Military Origins of Letterman Jackets Before letterman jackets became a symbol of high school pride, they were actually born on the battlefield. Here’s a little-known fact: The classic wool-and-leather design we know today was inspired by 19th-century military uniforms specifically, the heavy wool coats worn by cavalry soldiers....