Possible Clues:

• Wear it with tails
• 12 and 11's gone to the pub, it doesn''t say where
• Tossing of pennies: heads and tails, heads... and tails!
• Wear for formal occasions, which includes work
• Capital investment that involves work
• Astaire/Rogers musical
• Man's headgear worn with formal dress
• 1935 film starring Fred Astaire and Ginger Rogers
• Leading hotel on a budget finally getting suitable cover
• Highest head-covering