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.
John F. Kennedy at 28 years old in 1946.
A 1930 painting of Edward, the Prince of Wales, in a Fair Isle sweater.
A still from Love Story with Ryan O’Neal and Ali MacGraw.
A look from the Polo by Ralph Lauren collection of 1997.
Men of the 1961 class at Deerfield Academy in madras jackets.