Here is a selection of paintings through out history that involve hats.

 

Pablo Picasso (1902) Self-Portrait
Pablo Picasso Self-portrait 1902
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Edgar Degas Portraits at the Stock Exchange
Pastel on paper, pieced and laid down on canvas.
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Monet, The Terrace at Sainte-Adresse
Oil on canvas, 38 1/2 x 51 1/4, 1867
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Meissonier "1814"
"1814", Meissonier, 1813-1891. Louvre, Paris.
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Be A Good Boy
Karl Rossinsky. Israel, 1969. Photograph.
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The Vanishing Three Gorges
1991. Karl Rossinsky. Photograph.
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Thomas Gainsborough Portrait of Mrs. Siddons
Here is an English portrait painter whose name is synonymous with the lady's hat style that he is famous for painting!
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Whistler: Portrait of My Mother
James Whistler: Portrait of My Mother
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Van Gogh (1888) Self-Portrait with a straw hat
Van Gogh painted at least twenty-four self-portraits in Paris between March 1886 and February 1888, including seven in which he wears a straw hat.
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Cuernavaca Bakery
Cuernavaca Bakery, 1972. Karl Rossinsky. Photograph.
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Rembrandt, Saskia in a Red Hat
Oil on Panel, 39 1/2 x 31 in., c.1634-42
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Marc Chagall, The Green Fiddler
Oil on canvas, 195.6 x 108 cm., 1918.
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Louis Choris, Exotic Subjects
French artist Louis Choris's depiction of San Francisco Mission Indians, 1822.
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Francois Boucher, Madam Bergeret
Francois Boucher's portrait of Madame Bergeret, ca. 1750s. Madame Bergeret is hoding her "Bergere" straw hat, also known as the "Shepherdess," "Milkmaid", or "Skimmer."
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Toulouse-Lautrec, Le Divan Japonais
Toulouse-Lautrec poster, "Le Divan Japonais," 1892.
This Toulouse-Lautrec poster depicts Jane Avril and Edward Dujardin in "Gay 90s" Paris.
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Patrick LoCiero, The Traveler
Oil and Collage on Paper
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Eastman Johnson, Woman Reading
Eastman Johnson, Woman Reading. Oil on Board, ca. 1974.
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Auguste Renoir (1881)Two Sisters On the Terrace
Two sisters (On the Terrace) Oil on canvas.
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Auguste Renoir's (1876) Dance at Moulin de la Galette
When boaters, toppers or bowlers were worn by gentlemen dancing on a summer evening in Paris
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Max Ernst (1920) The Hat Makes the Man
Cut and paste paper, pencil, ink, and watercolor on paper.
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Rubens The Coronation of Marie (detail)
Detail from "The Coronation of Marie", Paris, 1625 (approx.)
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