Why did it happen?
As you can imagine, a revolt of this magnitude needed some pretty convincing motivations, beyond just a general feeling of discontent. Principally, there were three, the first of which was the Black Death. This terrible disease had arrived in England from the continent in 1348, and swiftly killed off about half of the English population. As a result, there was a shortage of labour, and workers naturally took advantage of this by demanding what the king called ‘excessive wages’. Feudal overlords such as barons and knights had no choice but to pay the increased prices for goods and labour.
Even the peasants, who received no pay and farmed the most meagre strips of land under normal circumstances, could demand more favorable employment terms. In 1349, King Edward III issued the Ordinance of Labourers, which fixed the wages and prices that people could charge at the pre-Black Death level. Having briefly tasted the possibility of becoming rich, the artisans and laborers were outraged, and in many cases simply ignored the law. This law impacted everyone below the knightly classes, widely sowing the seeds of rebellion, as the courts were flooded with prosecutions of those ignoring the Ordinance of Labourers.
Laws were even passed against sartorial aspirations. Not content with limiting the economic growth of the lower orders of society, in 1363 the powers-that-be also reissued old laws limiting what commoners could wear, lest they be confused for their social betters. These laws restricted wearing fur and shoes with points of 24-inches to the nobility, with merchants allowed only 6.5-inches of pointiness to their footwear. Peasants were also prohibited from eating all but the most basic of food. Such laws were an insult to most of the population without hereditary titles, pouring cold water on their dreams of social mobility.
If that wasn’t enough, there was also the matter of the Hundred Years’ War. The conflict, which formally began in 1337, was bloody, labor-intensive, and expensive, and rarely saw any decisive or permanent progress from either France or England. The origin of the conflict was the King of England’s dynastic claim to the kingdom of France, meaning that no one had any choice in the matter. Typically, wars were funded by the aristocracy, who technically leased their land from the king in exchange for the money and manpower to support royal expenditure, but in 1377 aristocratic coffers were near-empty.
This was disastrous, since the English were now on the back-foot, and needed to pay for more soldiers to defend the realm against the counter-attacking French. In early 1377, Parliament voted to raise funds through a Poll Tax, an unprecedented general levy on the entire population, from serf to baron. The people were unhappy, and decidedly poorer, but two years later were made to pay another Poll Tax. When all this money was hoovered up by the war effort, yet another Poll Tax, with even higher rates, was passed in 1381. The fuse was lit for a summer of rebellion.