What does Chaucer's descriptions of both the physical attributes and dress of the pilgrims reveal or suggest about their inner nature?

The apparel of the persons who are going to Canterbury is very revealing of the true character of these pilgrims.

In his Canterbury Tales, Geoffrey Chaucer utilizes "estate satire"; that is, he satirizes the abuses that occur with the three traditional estates of 

1. The Nobility


2. The Clergy


3. The Merchants and Peasants

It is the Clergy who receive the most satire, and deservedly so in the historical context. 

The knight is a noble man, "a worthy man," who has recently returned from battle as his "long armored shirt/And cotton tunic" are wet and dirty. Since he has not taken the time to change lest he miss the pilgrimage, the knight is sincere and certainly not vain.

His clothes reflect the impassioned youth, who sings or plays his flute all day. He is romantic:

His clothes were embroidered up and down, and bright
As meadows full of fresh flowers, red and white.

This man is a hunter, through and through; he wears green (it would be camouflage nowadays). He makes his own arrows from peacock feathers. He wear a St. Christopher, patron of travelers, medal.

• The Prioress

This nun is truly hypocritical as she is more concerned with worldly things. That she affects sophistication is apparent in her speaking French through her nose and her mannerisms as she daintily touches her food. 
Her vanity is displayed with the wimple of her nun's habit that is "carefully ironed," and the rosary that is around her neck is not the customary black of a nun's. Instead, it is more jewelry than it is part of her habit.

A pair of coral prayer beads was strung around
Her arm, great beads as green as anywhere found,
And hanging from them a brooch of the brightest gold,
Inscribed...Love Conquers All.

He also has a false pride and vanity that one in the religious life should not possess. He hunts, which is against the rules of his order, and, like the prioress, he is vain. Chaucer refers to him as a "lordly monk" who wears "lovely gray fur, the finest in the land." He fastens his monk tunic's hood with a golden pin. This is also like the prioress, who adorns her religious habit with the ornate rosary. In addition to these luxuries, the monk wears boots of the finest leather.

This man is supposed to live off the charity of others; however, he owns expensive clothes: He wears a luxurious cape "woven of couble twisted/Wool" in which he carries "generous presents for good-looking wives."

• The Merchant

Dressed in "many colors," and fancy clothes, the merchant hides his being in debt because he wishes to rise to the new middle class. He wears a "beavered hat from Flanders" and boots with "handsome buckles."

• The Lawyer

This man desires to join the ranks of the nobility through his own skills. Chaucer comments,

His clothes were modest, his coat was drawn
Around by a silken belt, brightly striped
Of the rest of his clothing I've nothing more to write.

The "man of law" invests his money in land, not clothes, but he wears good clothing.

• The Shipman

This is a coarse man of the sea, who pirates things and is always ready to fight. His clothes, like the man, are "coarse" and ill-fitting as they "flap onto his knees." With a coarse string around his neck he hangs his dagger and holds it under his arm for any time he may want it.

• The Wife of Bath ("A goodwife")

The clothes that she fashions from the cloth that she weaves are better than those woven by the Belgians and the Dutch, who were known for superior cloth. 

                                               ....Her stockings
Were red, full scarlet red and somewhat shocking.
....Her shoes were supple and new....
An outer skirt was wrapped around her hips
(Quite large), a pair of spurs on his feet.

The red stockings indicate the wealth of the "goodwife" because the red dye for them is made from a red beetle that can only be found in certain areas. Also, the color red symbolizes lust, and the Wife of Bath has had five husbands. Her outer skirt that she wears to protect her other clothes as she rides on her horse, is large and she has spurs on her boots, indicating that this lusty woman is a formidable force on her own.

• The Miller

Described as a "hefty rascal," the miller steals some of the grain he mills and cheats on his prices, but "could not be called, in truth,/A thief." As a decoy, he wears a white coat, and his hood is blue.

• The Steward

A crafty man who handles his lord's accounts, the steward also wears blue in his long overcoat and carries a rusty sword, and indication that it is not used as his pen and ledger are his weapons.