Ray-Ban Wayfarers
Sunglasses like these, which toe the line between slick and sporty, are universally flattering.
Ray-Ban ($139)
Navy Blazer
The prep-school staple is bulletproof cocktail-party attire—and the most versatile jacket you'll ever own.
Tommy Hilfiger ($600, sold as part of a suit)
Converse All-Stars
Embraced by legends from Johnny Carson to Kurt Cobain, low-top Chucks are as much a national icon as apple pie.
Converse ($42)
Striped Sweater
The modern embodiment of Kennedy-era nautical style: a gray-and-navy-striped cashmere or wool pullover.
Vince ($140)
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