Possible Clues:

• Hot tap dances in film starring Astaire and Rogers
• Film best bowler, perhaps
• Leading hotel on a budget finally getting suitable cover
• Tails partner to slippery path
• Piece of formal headwear
• Rich Uncle Pennybags wears one
• Royal wedding accessory
• Uncle Sam's headwear
• Monopoly token worn by Mr. Monopoly
• Item on Mr. Peanut's head