Roger Chillingworth certainly did not have any advantages over Hester when it came to his physiognomy. His age was not the matter, but his "studious" look may have been one of the few redeeming qualities that Hester may have found to tolerably accept a marriage proposal from him.
He is far from the studious man that he used to be, however, and his anger, hatred and hunger for revenge is evident in his body as well as in his soul. Hawthorne has a very interesting way to word Chillingworth's change. In chapter 14, he goes as far as to suggesting that the medicine man's diabolical ways are responsible for the way in which he has contracted a new image that is entirely detrimental.
Old Roger Chillingworth was a striking evidence of man’s faculty of transforming himself into a Devil, if he will only, for a reasonable space of time, undertake a Devil’s office...
Hawthorne (the narrator) offers that this transformation of Chillingworth does not make him look scary, or even menacing. All it does is to make him even more miserably sad than what he is. Even Hester has strong words for him.
“What see you in my face,” asked the physician, “that you look at it so earnestly?”
“Something that would make me weep, if there were any tears bitter enough for it,” answered she. “But let it pass! It is of yonder miserable man that I would speak.
It is clear that Hester can sense that all of this is a product of useless hatred. Of Chillingworth's own choices, which he should have never adhered to that way. Rather than letting go and moving on, he had to make a show of force so that his ego could be rectified.
Hester was alone 2 whole years thinking he was dead prior to getting with Dimmesdale. While she is not to be condoned for her actions, she has clearly not done anything to Chillingworth on purpose or to hurt him. This is why the author agrees that the entire thing is foolish.
This unhappy person had effected such a transformation by devoting himself, for seven years, to the constant analysis of a heart full of torture.
He certainly must be a very unhappy person to engage in such a campaign against someone he does not even know nor has done anything to him.
In chapter 14 of Nathaniel Hawthorne’s The Scarlet Letter, Roger Chillingworth’s appearance is described several times. In the post above, his appearance is described in terms of how Hester Prynne sees him. There is another key part of the chapter that occurs a bit later and uses Chillingworth’s appearance in a different way, showing the reader how Chillingworth actually sees himself.
Chillingworth has devoted his life, since coming to New England, to anonymously torturing Reverend Dimmesdale for committing adultery with his wife, Hester Prynne. However, the long-term effect of this behavior has changed Chillingworth from a caring, conscientious physician to an obsessed, evil manipulator.
In this chapter, Chillingworth is talking to Hester about his behavior toward Dimmesdale, admitting that he has become a “fiend” because of his evil actions. He sees an image of himself in “his mind’s eye”:
The unfortunate physician, while uttering these words, lifted his hands with a look of horror, as if he had beheld some frightful shape, which he could not recognize, usurping the place of his own image in a glass.
In this case, Chillingworth is imagining his own appearance, knowing that in some way it has changed to match the way he has changed over the years as he secretly works to make Dimmesdale miserable.
Throughout the novel, Hawthrone develops his description of Chillingworth from an older, weathered man to a twisted, almost demonic cariacature. Here is a quote after his change:
"But the former aspect of an intellectual and studious man ... had altogether vanished, and been succeeded by a eager, searching, almost fierce, yet carefully guarded look. It seemed to be his wish and purpose to mask this expression with a smile, but the latter played him false, and flickered over his visage so derisively that the spectator could see his blackness all the better for it. Ever and anon, too, there came a glare of red light out of his eyes, as if the old man's soul were on fire and kept on smouldering duskily within his breast..."
Hester sees his twisted features and the determined glint in his eye and immediately believes it is evil, even the devil, shining through on his visage. She understands at this point the length to which he will go to punish the man he believes to have wronged him by committing adultery with Hester.