Henry VIII in 1527

 A rarely seen painting of Henry VIII in 1527 (from the government offices at Downing Street).

So this is what he looked like when he began to court Anne Boleyn starting around that year.

It is by an unknown artist, but I suspect it might be by Lucas Horenbout/Hornebolte and his workshop.  

Horenbout was active at this period at the King's court, and the telltale shadow behind Henry indicates it was a work by the 'Cast Shadow Master', an artist who was probably Horenbout, according to art historian Roy Strong (see his 'The English Renaissance Miniature' book).