Possible Clues:

• Upper-class
• What Willy Wonka wears on his head
• 1935 film starring Fred Astaire and Ginger Rogers
• Monopoly token
• Capital investment that involves work
• Tossing of pennies: heads and tails, heads... and tails!
• Path to complex is by the milliner's presumably
• Astaire/Rogers musical
• Wear for formal occasions, which includes work
• Mr. Peanut prop