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Thomas Wilmer Dewing began creating decorative paintings of women in interiors around 1886, using this subject to explore formal issues of colour and composition. Like the American painter James McNeill Whistler, whose work he certainly would have known, Dewing was especially concerned with rendering subtle distinctions of hue and value. Although the sitters were intended to be anonymous, many of them have been identified as his friends or lovers. The woman depicted in Lady in Green and Gray is Gertrude MacNeill, an actress who frequently posed for Dewing between 1911 and 1917.
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