The first thing to note is that the person making this claim is Alec Cobbe, the very same Alex Cobbe who has since claimed to have identified a new portrait of Shakespeare in this same collection. Does this mean that this collection is a treasure trove of hidden gems? Or merely that he is a bit gullible?
Does the painting show someone, male or female, ‘dressed as a woman’? More to the point, have any of the experts actually claimed this? Alastair Laing certainly knows his stuff. But when Anthony Holden, who doesn’t, says that Laing ‘believed the portrait was not of a woman, but of a young man apparently dressed as a woman’, what weight are we to put on that word ‘apparently’? How strongly, if at all, does Laing agree with the idea that the sitter is dressed as a woman?
Personally, I think that the way in which the sitter is dressed is the most masculine thing about it. The outfit is more likely to be that of a man, while the long hair was a well-established male fashion of the time and men also wore earings. The doubt is instead the facial features, which could be - but far from necessarily - those of a young woman.
But one has to remember that the portrait is not a photograph. The face has literally been painted. (And we are looking at a photograph reproduced on a computer screen.) In any case, young men were often painted with pale skin and red lips.
As Laing says, identifications based on supposed resemblances are notoriously dodgy. But if one wants to make such comparisons, the obvious image to use is the Hilliard miniature in the Fitzwilliam. That at least dates from roughly the same time as the putative date of this portrait. And, despite what Cobbe and Holden claim, the resemblance is not at all ‘telling’. Any actual resemblances are things like the hair style, which simply underline that such things were fashionable among rich young men at that date. The facial features, on the other hand, are different. Particularly note the jawlines.
That leaves the claims about the provenance. So the Cobbes are related to the Wriothesleys. Fair enough. Except that such six-degrees-of-separation genealogical connections always need to be treated with some caution. Just because something could have descended through a family in a particular way does not mean that it did.
Strictly speaking, it is only the dedication of the book, a dedication which is not by Shakespeare, that is addressed ‘To Mr. W.H.’. This is why it isn’t obvious that ‘W.H.’ features in the Sonnets at all.