Upon his heed a Flaundryssh bevere hat;
His bootes clasped faire and fetisly.
(= Upon his head was a beaver-fur hat from Flanders / His boots were clasped nice and elegantly.)
Like many of Chaucer’s pilgrims, the Merchant’s clothes are a gateway to his personality. In this instance, his exotic clothes indicate his need to make a good first impression (like all merchants, or their modern descendants, salesman. Wonder why people whose job it is to sit behind a phone selling stuff wear suits to work— the answer’s in Chaucer).
His hat also projects an image of being well-travelled, and knowing his markets.
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