A New England Summer Style Almanac: A Gentleman’s Guide to Coastal Cool
From foggy ferry rides to yacht club dinners, here’s how to pack for a season defined by heritage fabrics, maritime polish and old-money ease.
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There’s a dress code in New England—you just won’t find it written down. It lives in unlined blazers, wind-scuffed loafers and linen that looks better after its third wash than its first. Whether it’s an oyster roast in Osterville or a foggy ferry to Vinalhaven, the well-appointed gentleman understands the assignment: effortless polish rooted in tradition. It’s a look that leans into linen, not logos; suede, not sneakers. Unlike the Riviera’s flash or the Hamptons’ high-gloss affectations, this is wardrobe minimalism with pedigree—preppy but not precious, heritage without costume.
That classic New England look hinges on tactile understatement: madras, seersucker and cotton poplin, the holy trinity of heritage summer dressing. These fabrics summon the season like church bells and clam shacks. But this edit trims the excess. No patchwork madras pulled from a prep school lost-and-found. No lobster embroidery on repeat. Instead: restraint. Garments that breathe, age well and carry from ferry deck to dinner table without fanfare. The fire-engine-red pants that somehow become acceptable north of the Sagamore? Skipped. But the sun-faded navy windbreaker in Bar Harbor? Absolutely.
This guide curates essential pieces that distill the region’s coastal clarity into fabric and form. They’re long-game investments—garments that will earn their keep year after year. Expect silhouettes that favor movement, textures that reward wear and a color palette rooted in salt air and sailcloth. Pack like you’ve done this before—even if it’s your first time booking a cottage in Kennebunkport instead of a room at the W.
The Ultimate New England Summer Wardrobe Packing Guide
- Vilebrequin Ultra Light Swim Trunks
- Polo Ralph Lauren Lightweight Linen Shirt
- Steele Canvas Nantucket Red Weekender Bag
- Moonstar Canvas PT Deck Shoe
- Brunello Cucinelli Logo-Embroidered Long Sleeve T-Shirt
- Loro Piana Federico Linen Camp Shirt
- Carl Friedrik Hybrid Trunk
- L.L.Bean Men’s Light and Airy Anorak Windbreaker
- Todd Snyder Italian Seersucker Double-Breasted Suit Jacket
- Orlebar Brown Horton Slim-Fit Polo Shirt
- Caswell-Massey Heritage Cologne Discovery Set
- Zegna Black Acetate Sunglasses
- Engineered Garments Blazer
- Mr P. Suede Sandals
- Tombolo x Boston Whaler Cabana Shirt
- Carpe Underarm Stick Antiperspirant
- Sebago Portland Artisan Boat Shoes
- Cartier Tank Française Automatic Watch
- Ocean Safe Mineral Sunscreen Tin
- Celine Homme Striped Cotton-Blend Sweater
- Loro Piana Silk And Cotton-Blend Jersey T-Shirt
- Onia Calder Seersucker Flat Front Shorts
- Vilebrequin Bohème Bucket Hat
- Buck Mason Loomed Linen OG-107 Fatigue Pant
- Montblanc Eyewearsquared Sunglasses
- Peter Millar Salem Salem Performance Short
- Frescobol Carioca Fabio Flip Flops
Vilebrequin Ultra Light Swim Trunks
A staple for coastal days that start with cold brew and end in saltwater, these Vilebrequin swim shorts are cut with a 2-inch inseam and crafted from lightweight polyester with a cotton lining (read: designed to dry fast and layer easily under a linen shirt or terry polo).

Polo Ralph Lauren Lightweight Linen Shirt
Few shirts nail American prep better than Ralph Lauren’s classic-fit linen. The relaxed cut works over swim trunks or tucked into pleated chinos, and the pastel palette looks best slightly rumpled. It’s the go-to piece for vineyard tours, seafood towers, or last-minute lobster rolls.

Steele Canvas Nantucket Red Weekender Bag
A love letter to East Coast tradition without slipping into cliché, this canvas weekender is built for the kind of packing that doesn’t involve rolling anything. Handmade by century-old Massachusetts brand Steele Canvas, it’s structured, durable, and dyed in that perfectly muted Nantucket red—a tone that reads “local” if you know, and “elevated” if you don’t.

Moonstar Canvas PT Deck Shoe
Built in Kurume, Japan, these deck shoes marry 1930s U.S. Navy function with Japanese craftsmanship. Vulcanized rubber soles provide grip and the cotton canvas upper keeps things cool and classic. Subdued colors like olive and ecru make them a versatile staple for New England days on land or sea.

Brunello Cucinelli Logo-Embroidered Long Sleeve T-Shirt
Knitted from near-weightless Italian cotton and finished with a barely-there sailboat logo, it reads like something picked up in Portofino but worn dockside in Nantucket. Quiet luxury, sure—but the kind only a seasoned summerer would recognize.

Loro Piana Federico Linen Camp Shirt
The Italian label’s signature linen feels featherlight but never flimsy, and the soft collar and generous cut make it the ideal piece for humid ferry rides or seaside aperitivos. The subtle nautical print and muted tones nod to coastal life without being overly literal.

Carl Friedrik Hybrid Trunk
For the man stretching Summer Fridays into a month-long residency, this 90-liter trunk delivers serious utility in one pretty package. A polycarbonate shell, aluminum frame, and leather trim house an 80/20 split lid, integrated dividers, and packing cubes for streamlined, three-week hauls. Smooth spinner wheels and TSA-approved triple locks handle ferry ramps and gravel drives with equal hardiness.

L.L.Bean Men’s Light and Airy Anorak Windbreaker
This featherlight windbreaker proves that utility and heritage can coexist in one smart, packable layer. The densely woven fabric blocks wind without weighing you down—perfect for unpredictable New England days where the fog rolls in faster than you can say “clam bake.” With its half-zip front, drawstring hem and kangaroo pouch (complete with a secure zip pocket), this anorak hits the sweet spot between function and nostalgia.

Todd Snyder Italian Seersucker Double-Breasted Suit Jacket
This double-breasted suit jacket from Todd Snyder reimagines seersucker without the stripes. Cut from Italian stretch cotton by the storied Subalpino mill, it delivers crisp structure with breezy ease, thanks to natural shoulders, a 6-on-4 button stance, and a partially lined interior. The creamy hue and ripple texture feel sun-faded yet sharp.

Orlebar Brown Horton Slim-Fit Polo Shirt
With a buttery-soft blend of mulberry silk and organic cotton, Orlebar Brown’s Horton polo moves beyond the basic pique standby. The open collar keeps things easygoing, while the ribbed texture adds the brand’s signature dose of sophistication.

Caswell-Massey Heritage Cologne Discovery Set
A whiff of legacy: This set includes three TSA-approved colognes from America’s oldest fragrance house. Newport delivers citrus and sea air; Greenbriar is woodsy and sage-forward; Sandalwood skews classic and dry. Perfect for weekend bags or glove compartments. When you don’t know the dress code, your scent should still speak volumes.

Zegna Black Acetate Sunglasses
With a sculptural silhouette and sculpted acetate frame, Zegna’s black sunglasses are what you reach for when a baseball cap won’t cut it. The convex grooves and fluid lines read as distinctly Italian, while the minimalist branding—just the 232 Road Mark on the temples and a subtle logo on the lens—keeps things polished.

Engineered Garments Blazer
This unstructured linen blazer distills the best of New England style into one wearable layer. Engineered Garments fuses American workwear pedigree with East Coast polish. The result: natural shoulders, breathable linen and patch pockets that keep things relaxed. Throw it over a white Oxford and khakis for a Wellfleet wedding, or pair with fatigue pants for impromptu cocktails in Chatham.

Mr P. Suede Sandals
A minimalist’s take on the summer sandal. Soft navy suede, Velcro straps, molded footbeds—the essentials, with Mr. Porter’s deft design. Whether you’re strolling the dock or ditching shoes after dinner, these add ease without sacrificing elegance. Proof that even your most casual shoes can look intentional.

Tombolo x Boston Whaler Cabana Shirt
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.

Carpe Underarm Stick Antiperspirant
New England summer humidity is no match for this dermatologist-tested antiperspirant, which works overnight to stop sweat before it starts. With a clean, powdery scent and non-greasy texture, it’s designed for guys who like their grooming extra effective when layering linen or lifting a mainsail.

Sebago Portland Artisan Boat Shoes
Hand-stitched in Maine and finished in Italian suede, these Docksides are heritage footwear with an upgrade. Their unlined construction keeps things breezy, while the siped rubber soles grip slick decks and stone wharves. They’re elegant without being delicate—perfect for everything from pulling traps in Kennebunkport to toasting sundown on a Vineyard terrace.

Cartier Tank Française Automatic Watch
Few watches carry the gravitas of Cartier’s Tank Française. The clean rectangular case, steel bracelet and automatic movement speak to decades of design authority. It’s elegant without being flashy—a timepiece for men who’d rather be noticed for their manners than their wristwear.

Ocean Safe Mineral Sunscreen Tin
Forget greasy formulas and chalky residue. This New England-made SPF 40 tin features just nine ingredients and a smooth, matte finish. It’s reef-safe, travel-friendly and fits easily in a tote or glovebox. Ideal for sailing days, garden parties, or bike rides down Ocean Avenue.

Celine Homme Striped Cotton-Blend Sweater
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.

Loro Piana Silk And Cotton-Blend Jersey T-Shirt
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.

Onia Calder Seersucker Flat Front Shorts
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.

Vilebrequin Bohème Bucket Hat
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 Loomed Linen OG-107 Fatigue Pant
These linen fatigue pants take cues from classic military silhouettes and reinterpret them for salt-air summers. The “full saddle” fit offers room where it counts, while the linen’s loomed texture nods to vintage utility wear. Details like corozo buttons and patch pockets elevate the design. - IMAGE

Montblanc Eyewearsquared Sunglasses
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.

Peter Millar Salem Salem Performance Short
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.

Frescobol Carioca Fabio Flip Flops
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.
