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The woman who commissioned this portrait was already forty years old and, in her day, would have been considered an old maid - although, as a sister of the enormously wealthy Boston merchant Nicholas Boylston, she would undoubtedly have made a good match. Copley, an experienced portraitist, handled the task with panache. Without seeking to give this confident woman a look of youth that would have defied all credibility, he concentrates on her charming vitality She sits for the artist, dressed in a silken negligee. This is intimate garb indeed.
In France, only the aristocracy had their portraits painted in such apparel. Yet it is the prerogative of the bourgeois Rebecca Boylston to adopt this dress as a sign of her confidence and imperturbable dignity. The thin fabric also gives Copley a chance to emphasize Rebecca's slender figure, showing her firm and youthful breasts beneath the satin sheen. At the same time, in the intelligent and slightly mocking gaze of her dark eyes, Copley suggests that this is a woman of experience. Six years later, Rebecca married a wealthy landowner who commissioned Copley to paint a second portrait of his beautiful wife.
The fact that Copley did not portray his model in the stiffly prestigious setting of a salon, but in a park, further underlines the natural charm of this millionairess. There is nothing contrived or affected in the way she holds the little basket of rose blossoms in her hands; it is almost as though she had just picked the flowers in the famous gardens of the Boylston villa. The slightly cramped Rococo attitude of Copley's earlier paintings succumbs here to a new and distinctly American directness and spontaneity.
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