George Strait looks like a man who has been to the Derby multiple times. His cappuccino-colored suit with an open dress shirt is enough to fit in among the stars in the Kentucky Derby celebrity suites, but casual enough to be comfortable and enjoy the races without bringing extra attention to himself. In this 2004 photo, Kid Rock and Travis Tritt both look on as Strait offers a little wisdom. Perhaps he's offering music advice, or just a pick on the ponies.