• The book cover of Preppy Cultivating Ivy Style

    Image Credit: Courtesy Photo

    The book cover of “Preppy Cultivating Ivy Style.”

  • A photo shoot from the blog Street Etiquette celebrated a modern-day African-American version of preppy

    Image Credit: courtesy of Street Etiquette.

    A photo shoot from the blog Street Etiquette celebrated a modern-day, African-American version of preppy.

  • John F Kennedy at 28 years old in 1946

    Image Credit: Getty Images

    John F. Kennedy at 28 years old in 1946.

  • A 1930 painting of Edward the Prince of Wales in a Fair Isle sweater

    Image Credit: Rizzoli

    A 1930 painting of Edward, the Prince of Wales, in a Fair Isle sweater.

  • A still from Love Story with Ryan O&#8217Neal and Ali MacGraw

    Image Credit: Photofest

    A still from Love Story with Ryan O’Neal and Ali MacGraw.

  • A look from the Polo by Ralph Lauren collection of 1997

    Image Credit: Courtesy of Ralph Lauren

    A look from the Polo by Ralph Lauren collection of 1997.

  • Men of the 1961 class at Deerfield Academy in madras jackets

    Image Credit: Courtesy of a Private Collection

    Men of the 1961 class at Deerfield Academy in madras jackets.

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