Possible Clues:

• Accessory for Mr. Monopoly
• 1935 Fred Astaire/Ginger Rogers film
• Original Monopoly token still in use
• Path to complex is by the milliner's presumably
• One of the original Monopoly tokens still in use
• Sounds like something you'd address to Patrick over hotel that's part of monopoly
• What Willy Wonka wears on his head
• Uncle Sam feature
• Upper-class
• Monopoly token