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Answer:
TOPHATS
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Formal wear
Formal headwear
Astaire props
They're often worn with tails
Astaire wear
They may be worn with tails
They may be seen with tails
They have high crowns
They got tipped at old-fashioned gentlemen's clubs
Tall head coverings
Quaint headgear
Props for Mr. Monopoly and Mr. Peanut
Many magicians wear them