Stirrup cups, so called because the contents are traditionally imbibed as a person departs when they already have their feet in the stirrups, harken back to the Roman era.
While there is evidence that it was a long-term tradition to offer when a departure was occurring, stirrup cups made particularly of silver were most popular in the 18th and 19th centuries when they were used by the aristocratic class during fox hunting. They would most often contain a port or sherry-based drink.
The silver stirrup cups frequently feature animal heads- in the 18th century they made in the form of hares and foxes, by the 19th century stags, deer and dogs were added.