The young Squire, twenty years of age, was the son of the Knight that accompanied him on the historic pilgrimage. 
He was undoubtedly what in later times we should call a dandy, for, "Embroideréd was he as is a mead, All full of fresh flowers, white and red. 

Singing he was or fluting all the day, He was as fresh as is the month of May.
While the Haberdasher was propounding his problem of the triangle, this young Squire was standing in the background making a drawing of some kind; for "He could songs make and well indite, Joust and eke dance, and well portray and write."

The Knight turned to him after a while and said, "My son, what is it over which thou dost take so great pains withal?" 

The Squire answered, "I have bethought me how I might portray in one only stroke a picture of our late sovereign lord King Edward the Third, who hath been dead these ten years. 

'Tis a riddle to find where the stroke doth begin and where it doth also end. 
To him who first shall show it unto me will I give the portraiture."

I am able to present a facsimile of the original drawing, which was won by the Man of Law. 
It may be here remarked that the pilgrimage set out from Southwark on 17th April 1387, and Edward the Third died in 1377.

See answer