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Answer:
BOATER
Possible Questions:
Straw hat
Summer hat
Yachtsman or hat
Yachtsman
Summer topper
Regatta entrant
Hat type
Gondolier
Yachtsman, e.g.
Wide-brimmed hat
Stiff straw hat
One making a wake
Yacht owner
Traditional barbershop quartet hat
Topper for a barbershop quartet member
Summer headgear
One who goes sailing
One punting, e.g.
One on board an outboard
One leaving a wake, perhaps
It typically has a ribbon around its crown
Hat style
Flat-top straw hat