Chaucer gives many descriptions of humanity in his prologue. Three that come to mind when discussing the concept of masculinity are the Knight, the Squire, and the Yeoman. We can see these styles of masculinity both in analyzing the descriptions of these men.
The knight embodies all that a medieval man should be. He follows the rules of chivalry and courtly love while being noble and successful in battle.
A knight there was, and he a worthy man,
Who, from the moment that he first began
To ride about the world, loved chivalry,
Truth, honour, freedom and all courtesy.
The speaker gives a lengthy list of the battles in which the knight has fought and is sure to mentioned his modest appearance on the pilgrimage.
His son, the Squire, represents the younger generation of man, the Renaissance man before the Renaissance begins in England. He is a "pretty" long-haired youth, who writes impassioned poetry, plays the flute and can dance.
Singing he was, or fluting, all the day;
He was as fresh as is the month of May.
Short was his gown, with sleeves both long and wide.
Well could be sit on horse, and fairly ride.
He could make songs and words thereto indite,
Joust, and dance too, as well as sketch and write.
He is admired by ladies for these traits but still maintains his respect and admiration for his father and for the battles in which he has fought.
The Yeoman is the servant to the Knight and the Squire. Not everybody is lucky to be born into royalty, so the Yeoman embraces the virtues of hard work and pride. He is meticulous about his arrows and unsurpassed in his level of expertise.
Of woodcraft knew he all the useful ways.
Upon his arm he bore a bracer gay,
And at one side a sword and buckler, yea,
And at the other side a dagger bright,
Well sheathed and sharp as spear point in the light;
Along with this, he is a loyal, God-fearing man.
Chaucer gives us three examples of men to admire during the days of The Canterbury Tales.