Dorothy Williamson was the granddaughter of George Millar Williamson, one of John Singer Sargent's first American patrons. Sargent painted Dorothy's portrait in London in 1900 and exhibited the work the following year at the Society of American Artists in New York. The New York Times critic wrote, "The portraits are many and good, led easily by little Miss 'Dorothy' in the Vanderbilt Gallery. . . . Seen near by, the red paint on the lips, the white paint on the little girl's hat seem quite misplaced, but as one steps back a bit the magic stroke takes place, the red lips are all right, the white ribbon is just right."

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