19. Connie Mack's Suits
Famed Appearance: In the Philadelphia Athletics dugout
In today's age, managers are obligated to wear a baseball uniform if they are going to observe the game from the dugout. Conversely, in the glory days of baseball, Connie Mack would park himself in the dugout as manager of the Philadelphia Athletics sporting fashionable duds that included tailored suits and matching hats. Legend has it that the only time his players saw him out of “uniform,” was during a 90 degree day in St. Louis where he loosened his tie a bit.