The Island Dress Code
Nantucket Style for Men
Faded reds, white linen, no socks. What men actually wear here — and every piece worth putting in the bag.
The Least Trendy Wardrobe in America
Nothing about how men dress on Nantucket has changed in fifty years, and that's precisely why it works. Walk down Main Street in August and you'll see the same four garments on men of every age: faded red or khaki cotton, a rolled-sleeve shirt, a sweater over the shoulders, and leather shoes with no socks. A grandfather and a twenty-two-year-old are often wearing the identical outfit, and neither of them looks out of place.
The trap is trying too hard. Head-to-toe brand-new nautical — the anchor-print shorts, the rope belt, the captain's hat — is the fastest way to look like you got off the fast ferry this morning. Island style is a small, worn-in wardrobe used well, not a costume.
Below: the five rules, then everything we've actually found worth buying, grouped so you can build the whole thing in an afternoon.
Buy it faded, or wear it until it is
Nothing on this island should look like it came out of the bag this morning. Nantucket reds are designed to lose their color, oxford collars are supposed to soften, and a canvas tote earns its stains. If you're choosing between two versions of the same thing, take the one that will age better rather than the one that looks better today.
One color story: navy, white, khaki, faded red
The whole island palette is four colors, and they all work with grey shingle and blue hydrangea. Add exactly one thing per outfit that isn't in that list — a green needlepoint belt, a madras pocket, a pair of tortoise sunglasses — and stop there.
Dress for six o'clock, not two o'clock
The temperature drops fifteen degrees when the fog comes in off the water and it happens fast. A quarter-zip, a cable-knit, or an unlined cotton sweater tied at the shoulders isn't an affectation here; it's the reason islanders never look cold in photographs.
No socks, but good shoes
Boat shoes and loafers are worn bare, which means the shoe itself has to be worth looking at. Real leather, real stitching, and a sole that can take wet cobblestone. Cheap boat shoes announce themselves within one summer.
The logo, if there is one, is very small
A one-inch embroidered whale, a small pony, a shop's name on the inside label. Anything larger belongs on the mainland.
Shirts, Polos & Sweaters
The top half of every outfit on the island: oxford cloth, washed linen, a performance polo for the boat, and the navy knit that comes out at six.
Men's
Polo Ralph Lauren Cream Polo Bear Crew Socks
The iconic Polo Bear in navy denim and stars-and-stripes knit into a soft cream cotton crew — the preppy little detail peeking out from a pair of boat shoes on a Fourth-of-July weekend.
Men's
Navy Nautical Anchor Crewneck Sweatshirt
The pull-on after a swim, the airport sweatshirt, the one your daughter steals — every coastal closet needs one.
Men's
Polo Ralph Lauren Men's Classic-Fit Pleated Hudson Chino Pant
Soft khaki cotton twill with a classic pleated front and a relaxed straight leg — the summer-through-fall trouser I'd pair with a navy blazer for the yacht club or a linen shirt untucked on the porch.
Men's
Vineyard Vines Men's Sankaty Performance Printed Polo (Blue Whale Print)
Cool hydrangea-blue chevron print in a moisture-wicking performance knit with the signature whale on the chest — the go-anywhere polo for the yacht club lawn, an afternoon on the boat, or dinner on the porch with white chinos.
Men's
Vineyard Vines Men's Solid Saltwater Quarter-Zip (White Cap)
The heavyweight cotton quarter-zip in crisp white cap with a heathered grey-lined collar and the little navy whale on the chest — the layer that lives on the back of a porch chair from Memorial Day through the first cold snap.
Men's
Vineyard Vines Men's Gingham Featherweight Performance Shirt
A soft sky-and-seafoam gingham in a featherweight quick-dry performance weave with a button-down collar — the shirt I'd wear untucked with khakis for a harbor-front lunch and tucked with a navy blazer by evening.
Men's
Lacoste Men's Sport Performance Polo (White)
Crisp white ultra-dry piqué with the green crocodile at the chest — the tennis-club polo that looks just as right over navy shorts at a clambake as it does on the clay courts.
Men's
Vineyard Vines Men's Terry Shep Shirt Quarter-Zip (Nautical Navy)
The original Shep Shirt in deep nautical navy with a heathered grey-lined collar and the little whale patch at the chest — the pullover that gets thrown on over swim trunks at dusk and never really comes off all summer.
Men's
Vineyard Vines Men's Collegiate Shep Shirt Quarter-Zip (Coral)
Sun-faded coral French terry with the signature quarter-zip placket — the warm-weather Shep Shirt that reads Nantucket red at golden hour over white shorts and boat shoes.
Men's
Lacoste Men's Regular Fit Cotton Blend Polo (White)
The everyday white polo in a soft cotton blend piqué with the green crocodile at the chest — the one that goes with jeans, khakis, and swim trunks alike.
Women's Apparel
Polo Ralph Lauren Cable-Knit Crewneck Sweater — Navy
The iconic Polo Ralph Lauren cable-knit crewneck in deep hunter navy with the tiny embroidered pony — the forever sweater I'd throw over a white tennis dress at sundown or knot around my shoulders for the ferry home.
Chinos, Shorts & Swim Trunks
Nantucket reds, khaki twill, and the six-inch trunk you can wear from the jetty straight to the raw bar.
Men's
Vineyard Vines Men's 6" Island Trunks (Jetty Red)
Sun-washed nantucket-red quick-dry nylon with a soft drawcord waist and a shorter 6" inseam — the classic Vineyard Vines trunk I'd throw in the beach bag for a swim off the jetty and wear straight to the raw bar after.
Women's Apparel
Vineyard Vines White Chino Shorts with Blue Scarf Belt
Classic crisp white cotton chino shorts finished with a breezy blue-and-white printed silk scarf belt — the polished preppy short I'd pair with a navy silk tee and leather sandals for lunch at the yacht club.
Shoes, Belts & Socks
Boat shoes worn bare, loafers for dinner, a needlepoint belt with something small and slightly ridiculous stitched across it.
Men's
Rainbow Sandals Men's Premier Leather Single Layer Flip Flop — Expresso
Broken-in premier leather that molds to your foot after a summer of wear — the island shoe that goes from the boat to the beach to a raw bar dinner without a second thought.
Men's
Sperry Men's Billfish 3-Eye Boat Shoe (Cognac)
Burnished cognac leather with rawhide lacing, a breathable mesh side panel, and a non-marking razor-cut sole — the boat shoe that gets better with every season of salt, sand, and cobblestone.
Men's
Merrell Men's Moab 3 Hiking Shoe (Granite)
Suede-and-mesh uppers on a Vibram sole — the do-everything trail shoe for Sanford Farm, the moors, and long dune walks out to Great Point.
Hats, Sunglasses & Small Things
The finishing pieces — a soft-brim cap that's already sweat-stained, tortoise frames, and whatever ends up in the pocket of the tote.
Women's Apparel
SOJOS Chunky Square Sunglasses — Glossy Black with Gold Detail
Oversized glossy-black chunky square frames with tiny gold-bar accents at the temples and a smoky gradient lens — the it-girl sunglasses I'd throw on with a white linen shift and a straw bag for a ferry-in morning on Main Street.
Women's Apparel
SOJOS Oversized Square Metal Sunglasses — Gold with Amber Gradient
Wire-thin gold square frames with a warm amber gradient lens — the quietly glamorous pair I'd tuck into a rattan clutch for cocktails on the lawn at the Whaling Museum benefit.
Women's Apparel
Retro Rectangle Sunglasses (Set of 2) — Black & Tortoise
A classic '90s-revival rectangle silhouette in glossy black and warm tortoise — the two-pack I'd stash one in the beach bag and one on the boat, because a good pair of sunglasses always disappears by Labor Day.
Bags
Vineyard Vines Navy Canvas Boat Tote Keychain (Whale Logo)
A perfectly scaled canvas boat tote keychain in navy and ivory with the embroidered whale logo — the sweetest little charm to clip onto your bag or house keys as a wink to the classic Vineyard Vines tote.
Accessories
Tortoise Brown Oval Retro '90s Sunglasses
The narrow tortoise-brown oval sunnies of an It-Girl's dreams — thin acetate frames, a delicate keyhole bridge, and rich caramel-brown lenses that give every outfit that vintage-Sofia-Coppola-in-the-Hamptons moment. The pair I'd slip on with a linen shirt and a straw tote.
Totes, Duffels & Weekenders
Heavy canvas with leather handles. It goes to the beach, to the ferry, and to the office, and it looks better every year.
Bags
Black Quilted Weekender Duffle with Matching Toiletry Set (3-Piece)
A soft-quilted black weekender with gold hardware, a matching cosmetic case, and a slim card wallet — the three-piece travel set I'd toss on the ferry for a long weekend on the island. Roomy enough for a linen dress, a swimsuit, and a stack of hardcover novels.
Also Worth a Look
The rest of the men's shelf — gifts, odds and ends, and the things that don't fit neatly anywhere.
Men's
Vineyard Vines Men's Shoreline Perfect Poplin Button-Down (Sky Blue)
Crisp sky-blue poplin with a soft button-down collar and the embroidered whale on the chest pocket — the shirt I'd wear with khakis to a harbor lunch and under a navy blazer for dinner in town.
Men's
Levi's Signature Gold Label Men's Relaxed Fit Jeans (Medium Wash)
A broken-in medium indigo wash in a relaxed straight leg — the honest weekend jean for beach-house chores, the ferry line, and a chilly bonfire on the sand.
Men's
Lucky Brand Men's Relaxed Straight Jeans (Lakewood Wash)
Soft vintage-wash denim with a relaxed straight leg and a lived-in fade — the jeans I'd pair with a navy Shep Shirt and boat shoes for a fall weekend on-island.
Men's
Barbour Men's Ashby Waxed Cotton Jacket (Olive)
Olive waxed cotton with a corduroy collar, brass snaps, and a tartan lining — the jacket that shrugs off a raw ferry crossing and only looks better after a few salty autumns on-island.
Kitchen
Fox Run Aqua Ceramic Whale Butter Dish with Lid
A little sea-glass aqua whale sitting on a scalloped wave dish — the cheerful two-stick butter keeper that makes a Sunday breakfast table feel like a summer cottage.
Questions We Get Asked
What do men wear on Nantucket?
The island uniform is unfussy: nantucket-red or khaki chinos (shorts above the knee in July, full-length after Labor Day), a white or blue oxford or a soft linen button-down with the sleeves rolled, boat shoes or loafers with no socks, and a navy quarter-zip or cable-knit sweater for when the fog rolls in around six. Nothing is new-looking. Nothing is logo-heavy except a small embroidered whale.
What are nantucket reds?
Nantucket Reds are cotton trousers and shorts in a dull brick-red canvas that fades, with wear and washing, to a soft salmon pink. The fade is the entire point — a brand-new pair reads as a tourist, a pair that has gone properly pale reads as a decade of summers. They were popularized by Murray's Toggery Shop on Main Street, and the look has since been copied by every East Coast label worth wearing.
Is there a dress code for dinner on Nantucket?
Most restaurants ask for 'resort casual,' which in practice means a collared shirt and long trousers — no swim trunks, no athletic wear, no flip-flops. A navy blazer over an open-collar shirt with chinos will get you into anywhere on the island, including the yacht clubs. Ties are essentially extinct except at weddings.
What shoes should a man pack for Nantucket?
Three pairs covers a week: leather boat shoes worn without socks, a pair of driving loafers or unlined suede loafers for dinner, and something you don't mind soaking — canvas sneakers or rubber-soled camp mocs — for the cobblestones after rain. Cobblestone streets destroy thin leather soles, so leave the dress shoes home.
What should men wear to a Nantucket wedding?
Summer island weddings are almost always tent-and-lawn affairs: a tan, light grey or navy suit in a breathable weave, a white shirt, and loafers. Seersucker and pale linen are welcome. Skip the black suit — it looks funereal against grey shingle and blue hydrangea, and it's brutal in August.
What is the difference between preppy and coastal men's style?
Preppy is about the crest — the tie, the crested blazer button, the deliberate clash of madras and stripe. Coastal is about the wear. Same wardrobe, but sun-faded, salt-stiffened, and slightly too soft, with the polish sanded off. On Nantucket the second one is the one that reads as local.
Keep Going
The Coastal Cottage Styling Guide
A 12-page Nantucket-inspired playbook — hydrangea-blue rooms, weathered cedar curb appeal, and the pieces I'd buy again tomorrow. Plus the weekly Sunday finds. Free, no spam.
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