What did Henry VIII look like?

At least at the start of his reign, Henry was quite attractive. Even allowing for flattery common in the 1500s, much of the praise of King Henry had root in truth.

Sir Thomas More calls him "the tallest" of his companions. His skeleton shows he was around 6'2. More goes on to say that "his strength fits his majestic body. There is fiery power in his eyes, beauty in his face, and the color of twin roses in his cheeks." He had broad shoulders, fair skin, auburn hair, and a small mouth.

He was trim in his youth because he was an avid hunter, athlete, and outdoorsman. His contemporaries generally agreed that he was the "handsomest prince ever seen" as the Venetian envoy wrote. All this praise seems to have gone to his head: Henry was vain, especially about his calves. Wise courtiers were those who stroked the ego of this beautiful and talented prince.

As he aged, his health and looks changed dramatically. By his sixth marriage, he was so obese he had to be hoisted into his bed or onto his horse with pulleys. His hair thinned. He grew a beard at times, which conveniently helped to hide his multiple chins. His ulcerated leg worsened and caused him great difficulty in mobility, which was especially hard for a proud prince to show.

One part of his appearance that never changed throughout his life: his love of ostentatious, expensive, flashy clothes.
Quotes from Alison Weir's Henry VIII: King and Court