23. The Great Escape
Year Released: 1963
Directed By: John Sturges
Starring: Steve McQueen, James Garner, Richard Attenborough, Charles Bronson
Many people would list Bullitt as Steve McQueen's most stylish film, but true devotees of the style icon would agree The Great Escape takes the cake. McQueen easily killed it in casual clothing because that's what he wore in his own life on a daily basis. From the all star cast to McQueen's famous motorcycle jump, it's obvious why so many Japanese heritage brands and magazines have referenced the film.