Possible Clues:

• Bowler alternative
• Part of Mr. Peanut's outfit (2 words)
• Formal headdress
• Monopoly piece
• 20's adaptations, with title he made up
• Fred Astaire signature item
• Signature wear for Astaire
• Cane accompanier, maybe
• It's associated with head and tails
• ''Cheek to Cheek'' movie