Possible Clues:

• Formal wear
• Astaire headwear
• Original Monopoly token still in use
• Sounds like something you'd address to Patrick over hotel that's part of monopoly
• One of the original Monopoly tokens still in use
• Uncle Sam feature
• Man's headgear worn with formal dress
• 1935 Fred Astaire/Ginger Rogers film
• 12 and 11's gone to the pub, it doesn''t say where
• Wear it with tails