People would be forced to wear bells in medieval times because they committed a crime, such as rape. They forced the rapist to wear the bell to warn others when they were in close proximity.
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In medieval times, a queen, king, prince, or princess would wear a crown. In current times, an actor playing one of these parts in a medieval re-enactment may wear a medieval styled crown.
he will wear dishrags
stuff
hats
they wore aprons for work