Yet it would be a mistake to view this painting only in terms of what comes next. Boy in a Red Waistcoat also reflects Cézanne's admiration for and connection to the past. He said himself that he "wanted to make of impressionism something solid and durable, like the art of the museums." He spent many hours teaching himself to be a painter by studying old masters in the Louvre. This boy’s pose, with hand resting on cocked hip, and the air of languid elegance that envelops his slender form are reminiscent of 16th-century portraits by mannerist artists.

Cézanne’s orchestrations of pattern and color, despite their astonishingly modern look, did not originate as an exercise in form and abstraction. Instead, they grew out of the artist’s response to his subject. He was, he said, seeking to realize a "harmony parallel to nature." Throughout his life Cézanne stressed that he painted from nature and according to his sensations. It was through color relationships that he made visible the fundamental character and connectedness of what he saw and felt. In the boy’s face and shirt the tones are mostly cool and remarkably varied—pinks, greens, lavenders, blues, purples—a contrast to the reds of his vest. Elsewhere color is more subdued. Autumnal tones in the background, some warmer, some cooler, all lower keyed, function like a moody bass line, tempering the more brilliant accents that play out over them.

The boy, a professional model named Michelangelo di Rosa, is garbed in the romantic costume of an Italian peasant, with floppy tie to match his striking vest. The round-brimmed hat, positioned high on his head gives him a certain naiveté, and the mussed bangs make him seem young, even vulnerable. He appears pale and pensive, his small mouth formed faintly, in Shapiro’s words, like the wings of a distant bird. Cézanne painted di Rosa several times while he was in Paris between 1888 and 1900. He must have found the young Italian an appealing subject, since he usually posed family members and friends.

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