Chaucer wrote The Canterbury Tales at a time of rapid social change in England. The Black Death had savagely depopulated the land, wiping out whole swathes of the population. Though there were fewer people, the demand for basic goods was still high, and so this created massive economic opportunities to be exploited. Thus was born a new middle-class: confident, wealthy, and increasingly powerful.
In "The General Prologue" Chaucer satirizes this new class as with other elements of contemporary society. He does this largely through a detailed physical description of the pilgrims such as the Merchant. The Merchant is one of the beneficiaries of the new economic system. He's made a lot of money and wants the whole world to see just how much he's made. He does this through wearing the very latest fashions, including a colorful cloak and a Flemish beaver hat. The pointed style of his beard is also very much in vogue.
With growing economic power comes political power, and we see this in the figure of the Man of Law. Though like the Merchant a member of the rising middle-class, the Man of Law is more modest in his dress and demeanor. Nevertheless, we're left in no doubt that this is a very wealthy, a very important man indeed. The growing mercantile economy requires more laws, rules, and regulations. In turn, this generates additional work for lawyers and judges such as the Man of Law. The Man of Law's made himself phenomenally rich through all the legal work he's taken on. So much so that he's now in a position where he appears busier than he actually is. In other words, he's so wealthy he can actually afford to turn down work.