Henry VIII had terrible taste in women!

I think people were just uglier back then. Especially royals who were slightly inbred.

A lot of our modern distaste for how they looked is due to fashion. In the Renaissance high, broad foreheads were very much in style. Women had their hair plucked to bring the hairline back farther and frequently plucked their eyebrows down to thin lines or removed them entirely to make their foreheads look bigger.

Probably not Grace Kelly and Gene because they didn't have high foreheads, plucked eyebrows, and they didn't have a certain look to them, that you would see in 15th and 16th centuries of women, that would make them conventional beauties.

What's remarkable is that prior to her failed pregnancies gaining her weight, Katharine of Aragon was considered one of the most beautiful princesses in the period -- to the extent that the cynical Thomas More even said as much to Erasmus in a letter, talking about her arrival in England in 1501.

But no, by modern standards, the women in the portraits aren't that attractive. (Though, if we'd never seen Megan Fox or Angelina Jolie or Grace Kelly or any other glamazon, would we find these women as unattractive?)

Paintings from the period aren't always representative of their subject, since metaphor and mythology was important, so the artist could have been doing a proper likeness -- or could have painted an impression based on the beauty standards of the day. Katharine's paintings interest me, since I know the most about her of all the wives -- there's a vague enough resemblance among them to give us a sense of what she looked like, but I still suspect some 'Madonna' influences in the works.

Henry also had an inflated sense of self and how gorgeous HE was, so... that should tell you something. ;)