Old money style on Nantucket has nothing to do with logos. It is faded red canvas, linen that has been washed a hundred times, and cable knits that have survived years of salt air. The island has an unwritten dress code that mixes East Coast prep with practical coastal clothing, and the whole point is that it looks inherited rather than bought. You do not need a ferry ticket to dress this way. What you need are crisp cottons, worn-in boat shoes, a light cashmere over the shoulders and a palette of navy, white, sand and soft red. The 30 outfits below are full head-to-toe looks, and most can be built from pieces you already own.
Packing an Island Week in One Bag
Most visitors arrive by ferry or small plane, and both make big luggage a nuisance. The good news is that old money dressing is naturally a capsule: a few neutral pieces that all work together. This is the core I build an island week around, then add one or two dresses:
- Bottoms: white jeans, khaki or white chinos, and one pair of faded red or navy trousers.
- Tops: a white button-down, a light blue oxford, a Breton stripe tee and a white tank.
- Layers: a navy blazer, a cotton cable knit and a light quilted or rain jacket.
- Shoes: boat shoes, a flat sandal, white sneakers and one pair of espadrilles or loafers.
- Dresses: a white eyelet or linen dress and one striped or seersucker sundress.
Everything here is navy, white, sand or soft red, so every top works with every bottom. That alone gives you more outfits than days on the island.
1. White Linen Dress With Espadrille Wedges
A white linen dress is the first thing I would pack for the island. Midi or knee length, pure linen or a blend, it looks polished without trying, and the texture already feels lived-in. Natural jute or cream canvas espadrille wedges give a little height. On cobblestones, though, I would keep the wedge low and wide; a narrow or tall one catches in the gaps between stones. A straw tote, small gold hoops and tortoiseshell sunglasses finish it, and it goes from a morning of shops to a harbor dinner without a change.
2. Navy Blazer With White Jeans And Penny Loafers
A navy blazer with gold buttons over crisp white straight-leg jeans is about as classic as this style gets. It reads nautical without tipping into costume, provided you keep everything else plain: a white crewneck tee or a thin striped tank. Roll the sleeves once or twice. Burgundy or cognac penny loafers, a silk scarf at the neck or in the pocket, and a structured leather crossbody finish it. The blazer has to fit at the shoulder; a boxy, too-big one is what turns this from inherited to borrowed. It suits a gallery evening or a harbor lunch.
3. Breton Stripe Top With White Chinos And Boat Shoes
A navy-and-white Breton tee with white chinos and brown leather boat shoes has been the island uniform for decades. I like the stripe slightly oversized, half-tucked, with chinos rolled to just above the ankle. A braided leather belt and a fine gold chain are what keep it from looking like a sailor costume. Boat shoes are made to be worn without socks, but bare feet in leather sweat; a pair of no-show liners keeps them fresh. Carry a canvas tote, and it covers a coffee run, antiquing and a casual clambake.
4. Cable Knit Sweater Over Shoulders With Khaki Pants
A cotton cable knit draped over the shoulders is one of the most recognizable old money gestures, and it is practical too, since the sea breeze picks up fast. Wear it over a white tank or striped button-down with tailored khaki chinos in a straight cut. Leather driving moccasins in tan or brown keep it walkable, but their thin rubber-nub soles wear fast on pavement, so they suit short walks better than long ones. Pearl studs, a thin belt and a rattan bag or lightship basket finish it for a garden party or an afternoon around Sconset.
5. Nantucket Red Pants With White Button-Down Shirt
Nantucket Reds, the salmon-pink canvas trousers that fade a little more with every wash, are the island's signature piece. With a crisp white button-down tucked in and the top button open, the shirt's structure sets off the softened canvas. Brown leather boat shoes or driving mocs, a braided belt, small gold studs and a straw or canvas tote are all it takes. The fading is the point, so I wash them in warm water and line dry rather than fighting it; a brand-new, bright pair looks far less convincing. A good outfit for daytime errands.
6. Seersucker Midi Dress With Straw Tote Bag
Seersucker is New England summer in a fabric. Its puckered weave holds the cloth away from the skin, so it breathes well in humidity and its crinkle looks deliberate rather than creased. A blue-and-white seersucker midi with a defined waist, a shirtdress or a self-tie belt, keeps the shape. Flat leather sandals or white canvas sneakers, a roomy straw tote, gold bangles and oval sunglasses finish it. Seersucker does not need ironing, which makes it one of the easiest things to pack. A throw-on dress for beach to brunch.
7. Linen Blazer With Tailored Shorts And Boat Shoes
A cream or sand linen blazer is the one jacket I pack for warm weather. Worn open over a white tank or a thin cashmere shell, with tailored shorts in navy or soft blush, it is relaxed but clearly put together. Leather boat shoes or suede driving moccasins keep it coastal rather than corporate, and a structured straw bag with minimal gold finishes it. Shorts with a blazer only work when the shorts are properly tailored, with a crease and a hem around mid-thigh or just above the knee. It suits a harbor lunch or a sunset sail.
8. Striped Sweater With White Jeans And Sneakers
A navy-and-cream striped sweater in light cotton or a linen blend is the layer I reach for on breezy evenings. Tuck the front loosely into high-waisted straight or wide-leg white jeans, then add clean white leather sneakers, a thin gold chain and tortoiseshell sunglasses. A canvas tote or woven market basket finishes it. Cotton sweaters stretch when hung, so I always fold them. It works for the farmers market, a ferry ride or a casual dinner by the water.
9. Eyelet Midi Dress With Woven Sandals
A white eyelet midi is the romantic side of island dressing. The cutwork adds texture and the cotton breathes. Look for a defined waist, through smocking, a tie or a gentle A-line. Flat woven leather sandals in tan or cognac let the eyelet do the talking, and pearl drops with a woven basket bag carry it from beach to dinner. Eyelet holes show what is underneath, so a lined dress or a slip in your skin tone is essential. Lovely for a garden party.
10. Polo Shirt With Madras Shorts And Leather Belt
A fitted navy or cream polo tucked into patchwork madras shorts is preppy island dressing at its most traditional. Madras is a light, handwoven-style cotton plaid whose colors soften and bleed slightly with washing, which is part of its charm. A slim leather belt with a brass buckle, brown leather sandals or suede mocs, small gold knot earrings and aviators complete it. Wash madras alone in cold water the first few times, since the dyes can run. Good for iced coffee in town or a cookout.
11. Shift Dress With Padded Headband And Ballet Flats
A shift dress in hydrangea blue, pale pink or butter yellow is the polished, feminine side of Nantucket style. The straight shape skims rather than clings, which makes it comfortable in warm weather. A padded satin or grosgrain headband keeps hair tidy in the wind and adds the preppy finish. Nude or metallic ballet flats, a small top-handle bag and pearl studs complete it. A shift needs room at the hip to walk easily, so I check the stride before buying. Good for a bridal luncheon or the wharf shops.
12. Tweed Jacket With Dark Denim And Riding Boots
For a crisp early-autumn day, a tweed jacket in herringbone or a subtle check, olive, brown and cream, is exactly right. Layer it over a fine-gauge cashmere crewneck and wear clean, dark straight-leg denim, never distressed. Tall brown leather riding boots and a silk scarf at the neck finish it. Tweed is warm and fairly wind-resistant, which is why it suits a blustery bluff walk. Riding boots need a jean slim enough to tuck in, or a straight leg worn over the boot. Ideal for a fall farm visit or dinner at an inn.
13. White Button-Down Shirt With Linen Trousers And Gold Jewelry
A well-pressed white button-down is the basic every old money wardrobe is built on, and with relaxed linen trousers in sand, cream or soft navy it looks right on the island. A full tuck reads more polished, a half-tuck more relaxed. I roll the sleeves just below the elbow, which makes any shirt look less stiff. Flat leather sandals or suede loafers, a few fine gold chains and a gold signet ring or slim watch finish it, with a woven crossbody. It moves from a morning meeting to a waterfront lunch.
14. Hydrangea Blue Sweater With White Shorts
Hydrangea blue has become a color story of its own on the island, and a soft cotton crewneck in that shade looks like summer there. Pull it over a white collared shirt so the collar and cuffs show. Tailored white shorts just above the knee, white canvas sneakers or espadrille flats, a thin gold bracelet and small hoops complete it. Pale blue suits most skin tones, but very cool, fair skin can look washed out in it near the face, so the white collar helps. Good for a bike ride or brunch in town.
15. Quilted Jacket With Straight Jeans And Rain Boots
The island weather turns fast, and a quilted jacket in olive or navy is the practical layer I always pack. The diamond stitching keeps the insulation in place, so it is warm without bulk. Wear it over a striped long-sleeve tee with straight medium-wash jeans and tall rain boots in a dark neutral. A canvas tote and a ribbed beanie finish it. Most quilted jackets shed light rain but are not fully waterproof, so on a real downpour day a waxed or rain-rated shell is the better choice. Good for a drizzly day of bookstores and museums.
16. Blue Oxford Shirt With Nantucket Reds And Penny Loafers
A light blue oxford cloth button-down softens and improves with wear, and it pairs naturally with faded Nantucket Reds. Cool blue and warm salmon pink balance each other well. Tuck the shirt in, add a brown belt with a brass buckle and cordovan or cognac penny loafers. A leather-strap watch, small pearls and perhaps a tortoiseshell barrette are enough. Oxford cloth is thicker than poplin, which is why it holds a collar and hides what is underneath. It suits a summer cocktail party or a porch dinner.
17. Floral Midi Dress With Straw Hat And Espadrilles
A floral midi with small, vintage-style blooms, roses, daisies or hydrangeas, brings out the romantic side of island dressing. Look for light cotton or crinkle gauze in a wrap or smocked-bodice shape. A wide-brim natural raffia hat gives real shade, and flat espadrilles in a matching neutral keep it comfortable. A straw crossbody and fine gold jewelry finish it. Small prints read more classic than large, bold ones, which is why I steer toward them for this look. It suits a beach picnic, a farm market or an outdoor island wedding.
18. Fisherman Sweater With Denim And Bean Boots
A chunky cream fisherman knit, based on traditional Guernsey designs, is the sweater for cool island evenings. Its dense knit and ribbed cuffs make it warm and wind-resistant. Pair it with straight medium-wash jeans and classic duck boots, which handle damp grass, sandy paths and boat decks. A leather watch, small studs and a low ponytail are all it needs. A real wool fisherman sweater can be itchy against bare skin, so I wear a thin long-sleeve tee under it. Ready for a beach bonfire or a foggy evening walk.
19. White Eyelet Dress With Pearl Earrings And Basket Bag
The white eyelet dress shows up on almost every island packing list because it looks festive without trying. The broderie anglaise texture keeps the all-white from looking flat. A midi with a fit-and-flare or soft A-line shape is the most versatile. Pearl drops give it the inherited-jewelry feel at the heart of this style, and a natural straw basket bag with flat tan sandals adds warmth. It is the dress for a bridal shower on the island, a festival garden party or a waterfront table. Check for a lining before you buy.
20. Gingham Pants With Oversized Button-Down And Cardigan
Blue gingham pants feel playful and still classic. Pair them with a crisp white oversized button-down loosely tucked at the front, and drape a mint or pale yellow cardigan over the shoulders, which also helps when the temperature drops. Flat sandals or white leather sneakers, a woven basket bag and gold studs finish it. Gingham trousers in a large check widen the hip, so I recommend a small check for most people. Ideal for a Saturday at the Nantucket Farmers Market, with flowers, honey and bread in the basket.
21. Navy Striped Sundress With Flat Sandals And Sunglasses
A navy-and-white striped sundress in a breezy A-line or relaxed shift captures island style in a single piece. A knee or midi length is the most versatile. Flat tan leather sandals, black or tortoiseshell sunglasses, a canvas tote and a few thin gold bangles finish it. If you plan to bike, which is the easiest way to get around the island, choose an A-line with room to pedal and avoid a narrow shift. It looks as good on a bike as at an outdoor cafe.
22. Cream Cape Coat With Chocolate Trousers And Knee Boots
Once autumn arrives and the crowds thin, a cream cape coat in soft wool or cashmere gives a dramatic, elegant shape. Layer it over a thin cream knit for tonal depth, then add chocolate brown tailored trousers and dark brown knee-high leather boots. A tan structured tote and vintage-style gold earrings finish it. Capes limit arm movement, so I carry a crossbody under the cape or a tote in the hand rather than on the shoulder. It suits a late-fall weekend and a foggy bluff walk.
23. Silk Scarf At Neck With Blazer And Tailored Shorts
A colorful silk scarf tied at the neck changes an outfit instantly and gives it a vintage, old money polish. Choose an equestrian, small floral or chain print and tie it in a small knot or a soft side bow. Against a navy linen blazer and white tank, with khaki or sand tailored shorts and suede driving mocs, it stands out nicely. Gold studs and a leather watch are enough. A real silk square holds a knot better than polyester, which slips loose in the wind. Good for an art show or a lighthouse tour.
24. Pastel Lilac Sweater With White Jeans And Raffia Flats
A soft lilac cotton or cashmere sweater adds a gentle color to white jeans. It feels fresh against the island palette of navy, white and sand. Tuck it loosely or let it skim the top of high-waisted white straight-leg jeans. Natural raffia slides, a woven clutch or small basket bag, pearl studs and silver bracelets finish it. Lilac is a cool shade, which is why I pair it with silver rather than gold. Good for a spring festival weekend, a seafood shack dinner or a sunset on a friend's deck.
25. Striped Button-Down Tied At Waist With Shorts
A blue-and-white striped cotton button-down tied at the waist shows a little skin and gives the shirt a new shape. Wear it over a white camisole or bandeau, with khaki or white tailored shorts at mid-thigh. Flat leather sandals or white sneakers, a straw fedora, aviators and a canvas tote complete it. The knot should sit at your natural waist, the narrowest point; too low and it adds width at the hip. Good for a bike ride along the island paths or the wharf shops.
26. Linen Matching Set With Gold Hoops And Slide Sandals
A linen set, a relaxed shirt with matching drawstring trousers in ivory or soft sand, is quiet luxury in its simplest form. The matching pieces make one long line, and linen stays cool. Wear the shirt buttoned or open over a thin white tank. Gold hoops and thin gold bangles warm up the neutral, and tan leather slides and a structured straw bag finish it. Elastic-waist trousers look more tailored when the top is left untucked over them. It suits an alfresco lunch or cocktails on a harbor patio.
27. Tennis Dress With White Sneakers And Visor
Tennis and pickleball are part of social life on the island, so a tennis dress fits right in. Choose white or pale blue with built-in shorts and a racerback or cap sleeve. Clean white leather sneakers, a white visor, a fitness watch and small studs are all you need. A light crewneck over the shoulders covers the walk after the match. Club courts often require mostly-white clothing, so check before you play. Good for courtside coffee or lunch at the clubhouse.
28. Cream Knit Top With Tailored Trousers And Structured Bag
A fine-gauge cream knit, a sleeveless shell, a cap-sleeve cashmere tee or a light merino crewneck, is one of the hardest-working pieces in this style. Tuck it into straight-leg tailored trousers in warm beige or soft navy, pleated or flat-front. Nude suede loafers or low block-heel sandals, a tan or black structured top-handle bag, a slim gold watch and fine chain earrings finish it. Merino handles warm days better than people expect, since it breathes and resists odor. It goes from a work meeting to a dinner reservation.
29. Boatneck Cotton Sweater With Cropped Chinos And Espadrilles
A white or navy boatneck sweater has a sailor history in its wide neckline. With cropped chinos that end just above the ankle and flat espadrilles in canvas and jute, it looks light and summery. A braided leather belt, small gold knot earrings, a chain bracelet and a woven crossbody finish it. A boatneck shows the collarbone, so it suits narrow shoulders particularly well; on broad shoulders it can widen the frame. It is right for walking the docks or a harbor lunch.
30. Nantucket Reds With Navy Polo And Braided Leather Belt
Every conversation about island style ends with the most iconic garment. Faded Nantucket Red pants, softened to a dusty salmon, with a classic navy polo is old money dressing in its plainest form. The polo should fit close but not tight, with a clean collar and no logo. A braided leather belt links the red and the navy, and brown boat shoes or penny loafers finish the base. A leather-strap watch, pearl studs and a canvas belt bag or crossbody keep it practical. This is the outfit that looks like you have spent many summers here.
Fog, Wind and Cobblestones
Island summers are milder than people expect. Daytime highs usually sit in the 70s, but wind off the water and evening fog can make it feel much cooler, and evenings often drop into the low 60s. That is why so many outfits here include a sweater over the shoulders; it is a practical habit before it is a style.
The cobblestone streets in town are hard on shoes. Thin heels and narrow wedges catch between the stones, and slick leather soles slip when the stones are damp. I stick to flat sandals with a rubber sole, boat shoes, sneakers or a low, wide espadrille.
Salt, Sun and Leather Care
Salt air and sand are tough on leather. Boat shoes and loafers can develop white salt lines after a wet day, which wipe off with a damp cloth and a little diluted white vinegar before the leather is conditioned again. Suede driving mocs should stay away from wet sand altogether. Canvas totes and red trousers fade in the sun, which suits this style, but whites need a cool wash and drying out of direct sun to stay bright rather than yellow.
Why These Clothes Look Better After Ten Summers
Old money style on the island is less about what you buy and more about how long you keep it. Faded reds, sun-bleached linen and well-worn cable knits look right because they have been worn for years. The style is restrained: neutral palettes, natural fibers, shapes that do not shout. You do not need a house on the bluff to wear it. Start with one or two of these outfits, put your money into fit and fabric, and add slowly. In a few summers your own clothes will have that same worn-in look.
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