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 ...

This may be a very subtle way to tick off the preppy trend, but belting your baggy trousers gives them a whole new feel. Even more so if you tuck in your T-shirt and add a classic cardigan over ...

Today, the fashion designer and retailer launched a spring/summer line that re-envisions preppy wardrobe staples (think: white button down shirts and polo shirts) with a contemporary lens.

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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 ...