So I saw someone mention that Tom was regularly referred to as ‘handsome’ by Harry in HBP, and I decided to check how accurate that was.
And they’re absolutely right. Harry can’t seem to make a trip into the pensieve without thinking of Tom as handsome.
Chapter 13: The Secret Riddle
There was no trace of the Gaunts in Tom Riddle’s face. Merope had got her dying wish: he was his handsome father in miniature, tall for eleven years old, dark-haired, and pale.
Chapter 17: A Sluggish Memory
There on the threshold, holding an old-fashioned lamp, stood a boy Harry recognized at once: tall, pale, dark-haired, and handsome–the teenage Voldemort.
Harry recognized Voldemort at once. His was the most handsome face and he looked the most relaxed of all the boys.
Chapter 20: Lord Voldemort’s Request
He was plainly dressed in a black suit; his hair was a little longer than it had been at school and his cheeks were hollowed, but all of this suited him; he looked more handsome than ever.
Harry thought he saw a red gleam in his dark eyes. His greedy expression was curiously mirrored on Hepzibah’s face, except that her tiny eyes were fixed upon Voldemort’s handsome features.
His features were not those Harry had seen emerge from the great stone cauldron almost two years ago: they were not as snake-like, the eyes were not yet scarlet, the face not yet masklike, and yet he was no longer handsome Tom Riddle.
“I won’t say a word, sir,” said Riddle, and he left, but not before Harry had glimpsed his face, which was full of that same wild happiness it had worn when he had first found out that he was a wizard, the sort of happiness that did not enhance his handsome features, but made them, somehow, less human.
To put this into perspective, the word handsome is used 12 times by Harry to describe people. Harry uses it 4 times to describe people who aren’t Tom, and once to describe Tom’s father.
But he uses it 7 times to describe Tom.
He also refers to Tom as handsome once in DH.
Chapter 19: The Silver Doe
Behind both of the glass windows within blinked a living eye, dark and handsome as Tom Riddle’s eyes had been before he turned them scarlet and slit-pupiled.
And while I’m at it, lets examine Tom regarding Harry ‘hungrily’ in CoS.
Chapter 17: The Heir of Slytherin
All the time he spoke, Riddle’s eyes never left Harry’s face. There was an almost hungry look in them.
There was an odd red gleam in his hungry eyes now.