The biggest acting role Duke Ellington ever had was his earliest, in 1929's Black and Tan. By then the sun was setting on the Jazz Age that Ellington had helped mint with his music, and his later work in film was reduced mostly to cameos and scoring. But in his debut, Ellington displayed the style sense that made him a fashion touchstone (in clothing as well as music) of the Roaring Twenties. He rarely appeared in photos without a waistcoat undergirding his suits. When he wore a tux, he turned it out, wearing long tails and sometimes a top hat. It would look garish on anyone else, but on an icon like Ellington it evokes the era of American history the Duke defined, when the money was plentiful, the parties never stopped, and the jazz played all night.—JOHN THOMPSON
* When in doubt, stick with what you know. Duke's foolproof standbys: double-breasted, wide-lapeled suits and overcoats that gave him a consistently strong, confident air.
CHECK IT OUT, DUKE ELLINGTON MADE GQ MAGAZINES LIST FOR THE MOST STYLISH MEN OF THE PAST 50 YEARS. CHECK OUT THE FULL LIST!