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Compared to his earlier paintings, Vermeer's brushwork in The Wine Glass is subdued, while the faces and clothes of the figures are depicted with wide smooth outlines. Only in the tapestry of the tablecloth and the window glass did the artist apply finely detailed, linear brush strokes. At the time Vermeer was not the only Dutch artist attempting to develop the ideas of De Hooch; contemporary paintings from Jan Steen, Gerard Ter Borch, and Frans van Mieris the Elder also display a refined technique.

The painting shares elements with other Vermeer works. The Girl with the Wine Glass (1659–1660) portrays two men, but in common with The Wine Glass it has a woman seated at a table with a glass of wine, and the tiled floors and stained-glass windows in both are very similar. The same wine pitcher appears in an earlier Vermeer, A Girl Asleep (1657).

The Wine Glass is a transitional work, and as such, is not commonly viewed as one of Vermeer's finest.