Sibylla dates to at least 1895, when it was shown at the London (Linked Ring) Salon of 1895.  Annan, who was also very interested in the framing, presentation and hanging of his work,  incorporated a black framed border etched into the copper plate surrounding this portrait. An anonymous writer in the publication Photograms of ’95 writes about a grouping of Annan portraits, including Sibylla:

“Mr. Annan’s portrait studies Sibylla (167), A Lady in Brown (161), and Margaret (176), are curiously interesting.  In them he has managed to obtain no little of the repose and distinction of a really fine portrait.  Much that is his own peculiar quality could only be successfully imitated by photographers equally accomplished as technicians, and equipped with no less artistic knowledge…”  1.

1.  J. Craig Annan: Selected texts and bibliography : Edited by William Buchanan : Clio Press : 1994 : p. 58