Rugby shirts, for example, started getting worn off the pitch in the 1950s, and John F. Kennedy popularized the New England preppy look in the 1960s by wearing chinos, Oxford shirts, polo shirts ...

Their definition is far different from your pearls and cable-knit sweaters. When I think of “preppy” fashion, Lilly Pulitzer and pearls come to mind. But if you ask Gen Alpha, you’ll likely ...

This might be the most adaptable clothing item when it comes to layering ... and though we love them on their own, they look uber-preppy in the best way under a cream cable knit or a suede ...