Winston is based on the Electro Motive Division F Series of Diesel Locomotives (he's an F7), built from 1939 to 1960. Even though his paint scheme doesn't have an actual basis, many people compare it to the Atchison, Topeka and Santa Fe (ATSF, or simply Santa Fe) "Warbonnet" passenger scheme.
@xxMilenariaOwOxx John E. McCollum for his song "Santa Fe All the Way" (Press Space and B)