I am not too sure if this has been done before, but here is a book series based on the wives of Henry VIII. I really love these covers as you can tell how much effort the artist has put into them.
Firstly, we have have the accurate Tudor fashion in the style that the individual wives favoured most and the startling likeness that each lady has to her portrait.
Secondly, the artist has taken into consideration the image of Henry as we see him gradually age as he moves onto another wife - we see him first as a young, viral man at the beginning of the series to the old, lecher that he became.
The only thing I would suggest that would have been a great detail would have been to lose the beard when he was married to Anne Boleyn as she detested beards and made Henry shave it off, which was why he (like the petulant child he was) grew it back after her execution and refused to shave it off, possibly to spit her. It also would have been better to make him slightly skinnier whist being with Jane and Anne Boleyn as he only gained weight after Jane died, but then the one with Anne might just be his jacket bulking him up. Another good detail would have been to make Anna von Cleves blonde, instead of light brown, but other than that the depiction of the Tudor King is spot on.
Lastly, I really liked the fact that you had the prominent wife in his life at that particular moment next to him, while the other wives waiting patiently in the shadows for Henry to take notice of them and the fact that those wives are dressed in the fashion of the prominent wife, which I think is a good idea as the Queen would have been the one to lead the fashion that her ladies would follow and then when you see the “shadow” wives feathered in their books, they are dressed in their own favoured fashion.
All in all, a really thoughtful cover design and I only wish that novels now a days would take the time and add the details that really pull the story together, I mean sometimes you can see historical novels, but the woman is wearing the wrong style of fashion for that time period the book is featured in.