Letterman jackets trace their roots to Harvard in 1865, when the baseball team sewed a bold “H” onto heavy wool sweaters to mark athletic achievement. By the 1930s, those sweaters had evolved into the classic wool-and-leather varsity jacket—practical on the field, but soon symbolic of pride, belonging, and status across American campuses. Worn first by athletes, the jackets became stitched into a broader story of tradition: the Ivy League as a cultural force, both deeply entrenched in hierarchy and, as historian Stefan Bradley notes, contested by student protest and civil rights struggle. Today, whether worn vintage or remade by brands from Ralph Lauren to New Balance, the varsity jacket remains layered with meaning—a garment caught between nostalgia and reinvention, between the institutions it once represented and the individuality it now signals.