A New England Summer Style Almanac for the Modern Man

Gentlemen, adjust your bucket hat and tilt your aviators just so. We’re about to embark on a sartorial odyssey through the hallowed summer havens of America’s blue-blooded elite. New England—that paragon of old money, Ivy League legacies and shingle-style manses with more history than your family tree—isn’t merely a destination. It’s a state of mind and a masterclass in the art of understated opulence.

Imagine nursing a G&T on the wraparound porch of the Ocean House in Rhode Island, or perhaps you’re navigating Edgartown’s cobblestone labyrinth, a butter-soaked lobster roll in one hand, a weathered copy of Moby Dick in the other. Now, what fashion choices have you made? If your ensemble doesn’t evoke the spirit of a young JFK fresh off his sailboat, we have some work to do. The art of New England summer dressing is a delicate balance between prep school polish and salt-air nonchalance. It’s a paradoxical pursuit—you want to look like you’ve inherited both your...