A frontal ink portrait of a man wearing glasses — the first spectacles in the entire portrait sequence across nearly 400 drawings. The glasses are drawn with the ink's bold line: rectangular frames sitting squarely across the face, the bridge over the nose, the temples running back to the ears. They give the face an immediate period specificity — heavy dark-framed mid-century eyeglasses — and a slightly earnest, bookish character.
The face beneath the glasses is well-observed: the brow above the frames carrying their own emphatic marks, the eyes behind the lenses drawn small and slightly recessed, the nose below the bridge broad and correctly placed. The mouth is closed, the expression one of neutral watchfulness — the habitual expression of someone accustomed to being looked at through glass.
The hair above is described with a few parallel marks indicating a side part, the overall head shape broad and square. The ears are drawn with their characteristic specificity at each side of the face, the frames' temples connecting to them. The collar and jacket below are given briefly — open collar, jacket lapels, the sitter apparently in ordinary clothes.
In a collection that has drawn hundreds of faces, this is the first time someone has been drawn wearing glasses. The glasses function compositionally like the mustache in the self-portraits, or the turban on the model — a specific, identifying formal element that makes the face particular rather than generic. Sidney observed it and drew it.