Possible Clues:

• Accessory for Mr. Monopoly
• Original Monopoly token still in use
• Path to complex is by the milliner's presumably
• Man's headgear worn with formal dress
• One of the original Monopoly tokens still in use
• Sounds like something you'd address to Patrick over hotel that's part of monopoly
• Uncle Sam feature
• What Willy Wonka wears on his head
• Astaire/Rogers musical
• Wear it with tails