01
Start with olive
The waxed jacket supplies the only strong color. Keep every other piece blue, khaki, white, navy, or cognac.
Shop This Look
Nantucket Fall Style for Men
Olive waxed cotton, a blue button-down, proper khakis, and worn-in boat shoes — the quiet New England uniform for the ferry, the wharf, and dinner in town.
The Coastal Fall Capsule
Seven pieces. Every fall weekend covered.
The Barbour Ashby is the anchor: weatherproof enough for a raw harbor morning and polished enough for lunch in town. Add sky-blue poplin, classic khaki chinos, cognac Sperrys, a navy quarter-zip, and the black weekender for an unfussy capsule that improves with wear.
Exact Linked Products
Shop the Nantucket Fall Look
Men's
Barbour Men's Ashby Waxed Cotton Jacket (Olive)
$400·at Amazon
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.
Men's
Vineyard Vines Men's Shoreline Perfect Poplin Button-Down (Sky Blue)
$110·at Amazon
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
Polo Ralph Lauren Men's Classic-Fit Pleated Hudson Chino Pant
$98·at Amazon
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
Sperry Men's Billfish 3-Eye Boat Shoe (Cognac)
$110·at Amazon
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
Vineyard Vines Men's Terry Shep Shirt Quarter-Zip (Nautical Navy)
$135·at Amazon
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
Polo Ralph Lauren Men's Classic Fit Oxford Shirt (White)
$98·at Amazon
The white cotton oxford every coastal closet is built around — rolled at the sleeves over swim trunks, tucked under a navy blazer for dinner in town.
Bags
Black Quilted Weekender Duffle with Matching Toiletry Set (3-Piece)
$78·at Amazon
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.
The Full Closet
Every Men’s Piece We Carry
Shirts, polos, quarter-zips, chinos, jeans, jackets, boat shoes and sandals — the whole preppy New England lineup, each one linked to the exact piece.
Men's
Nautica Men's Classic Fit 8.5" Deck Short — Indigo
From $32·at Amazon
A washed indigo cotton short with a flat front and a true 8.5" inseam — the one he'll wear with a rumpled linen shirt and white sneakers from the boat to dinner all summer.
Men's
Polo Ralph Lauren Cream Polo Bear Crew Socks
$18·at Amazon
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
Rainbow Sandals Men's Premier Leather Single Layer Flip Flop — Expresso
$62·at Amazon
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
Navy Nautical Anchor Crewneck Sweatshirt
$25·at Amazon
The pull-on after a swim, the airport sweatshirt, the one your daughter steals — every coastal closet needs one.
Men's
Vineyard Vines Men's Sankaty Performance Printed Polo (Blue Whale Print)
$89.50·at Amazon
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 6" Island Trunks (Jetty Red)
$79.50·at Amazon
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.
Men's
Vineyard Vines Men's Solid Saltwater Quarter-Zip (White Cap)
$125·at Amazon
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
$110·at Amazon
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)
$88·at Amazon
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 Collegiate Shep Shirt Quarter-Zip (Coral)
$125·at Amazon
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)
$98·at Amazon
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.
Men's
Lacoste Men's Classic Fit L.12.12 Pocket Polo with Contrast Tipping (Cream)
$110·at Amazon
Ivory piqué with a navy-tipped collar and cuffs and a neat chest pocket — the quietly perfect polo for a late-afternoon sail and dinner on the porch after.
Men's
Polo Ralph Lauren Men's Classic Cotton Crew Neck T-Shirt (3-Pack)
$45·at Amazon
White, soft harbor blue, and deep navy in pure cotton with the little embroidered pony — the layering tees that live under everything all summer long.
Men's
Levi's Signature Gold Label Men's Relaxed Fit Jeans (Medium Wash)
$34·at Amazon
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)
$89·at Amazon
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
Merrell Men's Moab 3 Hiking Shoe (Granite)
$110·at Amazon
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.
02
Choose texture over logos
Waxed cotton, Oxford cloth, brushed chino, and weathered leather create quiet luxury without looking new or showy.
03
Pack one extra layer
A navy quarter-zip fits in the weekender and handles the temperature drop when the harbor fog comes in.