Henry in 1531 at age 40, two years prior to his marriage to Anne Boleyn
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Catherine of Aragon at age 16 or 17, still in her mourning dress. This portrait really shows her reddish hair.
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Don't know squat about the histrory but those are some of the best portraits I've seen, it seems like a lot of old pictures are rather crude or at least stylized so it's hard to tell what the people *really* looked like.