It was partly a nod to this that May Day featured milk maids and sweeps, decorated in their best, and dancing in competition with one another. Jack of the Green was a sweep invention to get the most coins from the crowd.

May be an image of 1 person

For some reason, this image often gets censored by Facebook, anyway - medieval hiring fairs, often known as Statute Fairs or Mop Fairs, were a central part of the employment system in medieval England, and continued up to the 20th century.
The fairs would attract a grand array of labourers, from maids and milkmaids to ploughmen and shepherds.
Prospective employees would dress in their best attire and often hold symbols of their trade, a maid would be holding a mop, a shepherd would hold his shepherd'’s crook, a cowman, a lock of cow hair or a milking pail.
Employers would travel from surrounding areas, hiring these workers after negotiating terms of employment, including wages, food allowances, and living conditions. Contracts were usually verbal and witnessed by others at the fair, making them legally binding for a year.
Importantly, these fairs radically changed labour dynamics in England. They allowed labourers to sell their skills to the highest bidder and negotiate better working conditions. The competition among employers for skilled workers also led to an increase in wages, a concept fundamentally different from the feudal system that existed previously.