There aren’t that many portraits of John Donne, and one of the best, the one you see here, has been in various private collections and less than accessible. This portrait was painted in Donne’s twenties, around the 1590s, the period when Jonson said “Donne wrote wrote all his best poetry,” the era in which we think most of the love poetry was written. The portrait was almost certainly done with Donne’s supervision. It’s Donne done as a melancholy lover, complete with disheveled and pricey expensive lace collars undone, and a Latin epigram. Donne is wearing an exceedingly romantic black floppy hat, and there’s a certain earnest directness to his gaze that suggests the suffering lover. You can read about the portrait here, and you should because it’s interesting.
This is more than likely the portrait Donne described in his will and left to Robert Ker, later 1st Earl of Ancrum (1578–1654):
I give to my honourable and faithful friend Mr Robert Karr of his Majesties Bedchamber that Picture of myne wch is taken in Shaddowes and was made very many yeares before I was of this profession [i.e. a minister].
England’s National Portrait Gallery is trying to raise funds to buy the portrait for the Gallery’s collection. You can read about the appeal here, and donate, very easily even from North America. The National Portrait Gallery must raise £1,652,000 by the end of May.
While I’m on the topic of Donne, I want to point to this nifty .pdf chart you can download and print: John Donne on Maps and the Microcosm. There’s even intelligent commentary. It’s an effective and nicely done exploration of the two motifs, and quite useful in teaching. The broadsheet is a production of the University of Wisconsin’s The History of Cartography Project, which has a series of downloadable broadsheets on “Literary Selections on Cartography.”
ETA: The appeal was successful.