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 wardrobe and your WASP-y good looks, even if the reality involves more L.L.Bean than family crest.
From the rocky shores of Maine to the golden beaches of Cape Cod, not forgetting the exclusive enclaves of Nantucket and Martha’s Vineyard, each corner of this storied region has its own flavor. We’ve distilled the essence of New England style into a capsule wardrobe that’ll have you fitting in faster than the 45-minute flight from Teterboro. So, hoist your Nantucket Reds and polish those boat shoes. We’re setting sail on a how-to-pack New England summer fashion guide that will see you effortlessly gliding from beach to yacht club, from clambakes to garden parties. After all, in the land where Kennedys once tossed pigskins and Martha Stewart elevated the humble lobster roll to an art form, your ensemble should be nothing short of a Yankee magazine centerfold.