Conjure the spirits of Kennedys past with our magical packing guide to the Northeast's swankiest summer haunts.
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.
Nothing says “I’ve got a mooring in Marblehead” quite like this collaboration between Tombolo and the iconic Boston Whaler. This organic cotton terry cloth cabana shirt is as unsinkable as the legendary boats that inspired it. With chain-stitched details and custom embroidery, it’s the perfect layer for when the sea breeze kicks up during your sunset sail.
Imagine the lovechild of British tailoring and Italian exuberance taking a dip in the crystal-clear waters off Nantucket. These Orlebar Brown x La DoubleJ swim shorts are just that—a sartorial splash that’ll turn heads from Cape Cod to Martha’s Vineyard. The Whitsun print, a geometric riff on florals, is as eye-catching as a lighthouse beam, while the shorter swimsuit length says you’re not afraid to show a little leg (or a lot of confidence). Pair them with a button-up linen shirt for an easy cover-up.
A New England summer staple since its founding in Massachusetts in 1921, this Steele Canvas tote is the carry-all of choice for those in the know. Sturdy enough to haul your haul from the farmer’s market to the beach, it’s a silent nod to those who appreciate heritage craftsmanship. Just don’t use it to carry your dog—that’s what the family station wagon is for.
When your itinerary includes both urban exploration in Boston and a hike through Acadia National Park, Salomon’s Odyssey ELMT sneakers are your go-to footwear. Their technical prowess is masked by a design that wouldn’t look out of place at a trendy Seaport District bistro.
For those chilly Cape Cod evenings, this Celine sweater brings a touch of punk to your preppy ensemble. Its variegated stripes and loose fit say, “I might have gone to Phillips Exeter, but I spent my gap year following the Clash.” Pair it with skinny white jeans or tailored chinos for a look that works from Provincetown to Portsmouth.
When your day calls for transitions from yacht deck to country club terrace, reach for this Loro Piana crew-neckline tee. Its silk-cotton blend whispers luxury without shouting it, making it the perfect underpinning for your blazer or a standalone piece for more casual affairs.
This Beach Guy polo from The Elder Statesman brings West Coast cool to East Coast tradition. Its fine ribbing and contrasting collar make it the ideal choice for those Nantucket days when you want to stand out just enough at the Chicken Box.
These Gucci shorts prove that even your most casual moments can be infused with Italian flair. The contrast trim and subtle embroidery elevate them from mere loungewear to a statement piece worthy of your family’s private beach on Martha’s Vineyard.
Onia’s take on the classic seersucker short is as essential to your New England wardrobe vibe as a lobster bib. The flat-front design and quick-drying fabric make them perfect to throw on for impromptu dips in the Atlantic or long afternoons at the Newport Polo grounds.
No New England summer outfit is complete without a pair of statement sunglasses, and Montblanc’s squared frames fit the bill perfectly. Their Havana-colored acetate and green lenses add a touch of old-world sophistication to your summer style look, whether you’re watching the regattas in Newport or people-watching on Commercial Street in Provincetown.
Vilebrequin’s bucket hat is the thinking man’s sun protection on bright summer days. In understated mineral-dyed linen, it’s equally at home shielding you from UV rays at the Hyannis Port Yacht Club as lending an air of mystery as you peruse rare first editions in Edgartown.
Buck Mason’s linen fatigue pants are the sartorial equivalent of a well-worn copy of The Old Man and the Sea—rugged, timeless and hinting at adventures past. These are perfect for those casual Block Island bike rides or clambakes on the beach.
For the gentleman who takes his golf as seriously as his gin martinis, Peter Millar’s Salem shorts are a hole-in-one. Their moisture-wicking fabric and versatile cut make them ideal for eighteen holes at The Country Club, followed by cocktails on the veranda—just pair them with a button-down or a polo shirt and cardigan.
Bring a touch of Brazilian flair to your Nantucket beach day with Frescobol Carioca’s Fabio flip flops. Their Copacabana-inspired soles will leave a distinctive mark in the sand as you stroll along Cisco Beach, hinting at your worldly adventures beyond the ACK.
