Sidney's own title is written at the upper left: "Woe" — one of the most emotionally direct titles in the collection, and one that immediately reframes the portrait it names. A woman is seen in three-quarter view, her face turned slightly away, her expression one of quiet sorrow or gravity. The eyes are downcast or closed, the brow slightly furrowed, the set of the mouth suggesting something held in rather than expressed.
The drawing technique here is Sidney's most fluid ink line — large, single-stroke contours that describe the face and hair in a few confident passes. The hair, swept back and described in parallel arcs, has a quality of movement despite the stillness of the figure. The ear, visible at right, is adorned with what appears to be a looped or beaded earring — a small domestic detail that grounds the portrait in real life.
The title "Woe" does not explain the cause or context of the feeling — it simply names it. This is the emotional state Sidney saw or recognized in the subject, and found worth recording. The restraint of the single word — not "Grief" or "Sorrow" or "Sadness" but the older, starker "Woe" — gives the title a weight that suits the quiet gravity of the face.
This is one of only a handful of emotionally titled portrait drawings in the collection, and the emotion named here is one Sidney saw fit to preserve. Whether this is a person he knew in a particular moment, or a more general study, is unknown.