So when Chaucer tells us that the Merchant was a 'worthy man withal,' we can probably take that a bit ironically. In medieval England, to be in debt was a sign of weak morals. He manages to keep his head above water by borrowing more and more. Although he appears prosperous, we know that the Merchant is actually in debt.
The merchant's main motivation is 'th'encrees of his wynnyng' (General Prologue 277), or making money, and the military protection of trade routes that allows him to do so – these subjects are all he talks about. We know the merchant is the fashionista of the group because he's wearing a cloak of 'motley' (variegated, colorful pattern), a Flemish beaver hat, and has a forked beard, all of which were current fashions at this time period.
