Old money style on Nantucket isn’t about flashy logos or trying too hard—it’s a quiet language of faded Nantucket Reds, sun-bleached linens, and cable-knit sweaters that have seen a decade of salty breezes. The island has its own unwritten dress code, blending East Coast prep with coastal ease in a way that feels inherited rather than bought. Whether you are actually summering on the Grey Lady or simply channeling that hydrangea-lined, cobblestone-street energy from home, these 30 old money outfit ideas for Nantucket will help you nail the look. Think crisp cottons, weathered boat shoes, whisper-weight cashmere tossed over the shoulders, and a palette borrowed straight from the harbor at dawn. Every outfit here is a complete head-to-toe look you can recreate with pieces you likely already own or can easily find.
1. White Linen Dress With Espadrille Wedges
Picture stepping off the ferry in a breathable white linen dress that moves with the island breeze. A midi or knee-length silhouette in pure linen or a linen blend keeps things polished without feeling fussy. The fabric’s natural texture gives it that lived-in Nantucket feel right away. Pair it with a classic espadrille wedge in natural jute or cream canvas—the height is just enough to dress things up while keeping you comfortable on cobblestone streets. Add a woven straw tote, delicate gold hoop earrings, and tortoiseshell sunglasses for a look that transitions seamlessly from a morning spent browsing Main Street boutiques to a sunset dinner overlooking the harbor.
2. Navy Blazer With White Jeans And Penny Loafers
A navy blazer with gold buttons is practically a Nantucket uniform piece, and it looks especially sharp thrown over crisp white straight-leg jeans. The contrast feels nautical but never costume-y, striking that perfect old money balance between polished and relaxed. Roll the blazer sleeves once or twice for an undone touch that says you are not trying too hard. Underneath, keep it simple with a white cotton crewneck tee or a thin striped tank. Penny loafers in burgundy or cognac leather ground the look, while a silk scarf tied around the neck or looped through the blazer pocket adds a whisper of personality. Finish with a structured leather crossbody and you are ready for anything from a gallery opening to a harborside lunch.
3. Breton Stripe Top With White Chinos And Boat Shoes
This combination is the unofficial summer uniform of the island and has earned its status over decades. A navy-and-white Breton stripe long-sleeve tee—slightly oversized for a relaxed fit—paired with crisp white chinos creates an effortlessly classic silhouette. Roll the chino cuffs just above the ankle to show off classic brown leather boat shoes. The key to keeping this from feeling like a costume is in the details: a half-tuck of the shirt adds shape, a braided leather belt bridges the pieces, and a simple gold chain necklace keeps it feminine. A canvas tote bag slung over the shoulder completes a look that works for a morning coffee run, an afternoon of antiquing, or a casual clambake by the water.
4. Cable Knit Sweater Over Shoulders With Khaki Pants
There is something undeniably old money about a cotton cable-knit sweater casually draped over the shoulders. This styling move is iconic for a reason—it adds instant polish and provides a light layer when the sea breeze kicks up. Wear it over a simple white tank or a striped button-down, paired with tailored khaki chinos in a straight or slim-straight cut. Leather driving moccasins in tan or brown keep the look grounded and walkable. Small pearl stud earrings and a thin leather belt tie everything together without stealing focus. Grab a rattan handbag or a classic Nantucket lightship basket purse, and you have an outfit that feels pulled-together for a garden party, a daffodil festival, or a leisurely afternoon stroll around Sconset.
5. Nantucket Red Pants With White Button-Down Shirt
Nantucket Reds—those iconic salmon-pink canvas trousers that fade gloriously with every wash—are a cornerstone of island style. Originally created by Murray’s Toggery in the 1960s, they bring genuine heritage to any outfit. Pair them with a crisp white button-down shirt, tucked in neatly and with the top button undone for a relaxed feel. The shirt’s structure balances the pants’ softened, worn-in texture beautifully. Brown leather boat shoes or driving mocs complete the base, while a braided leather belt in a complementary tone pulls it all together. Keep jewelry minimal with small gold studs, and grab a straw or canvas tote for daytime errands. This outfit whispers Nantucket history without saying a word.
6. Seersucker Midi Dress With Straw Tote Bag
Seersucker’s signature puckered texture is practically synonymous with New England summers, and a midi dress in blue-and-white seersucker stripes delivers instant island charm. The fabric breathes in humidity and has a natural crinkle that looks intentional rather than wrinkled—perfect for a day that moves from the beach to brunch. Choose a silhouette with a defined waist, like a shirtdress style or one with a self-tie belt, to keep the shape flattering. Flat leather sandals or white canvas sneakers keep the look relaxed. A roomy straw tote bag, simple gold bangles, and dark oval sunglasses add the finishing touches. This is a throw-it-on-and-go dress that still looks thoughtfully styled for any casual island occasion.
7. Linen Blazer With Tailored Shorts And Boat Shoes
A linen blazer is the warm-weather layering piece that instantly elevates every outfit it touches. In a cream or natural sand shade, it pairs beautifully with tailored shorts in navy or soft blush for a look that feels intentional without being overly formal. The combination walks the line between relaxed and refined, making it ideal for a harborside lunch or an afternoon shopping trip. Let the blazer hang open over a simple white tank or a thin cashmere shell. Leather boat shoes or suede driving moccasins keep the vibe coastal rather than corporate. Add a structured straw bag and minimalist gold jewelry, and you have a complete look that takes you from a morning meeting at a café to a sunset sail with ease.
8. Striped Sweater With White Jeans And Sneakers
A lightweight cotton or linen-blend striped sweater in navy and cream is a Nantucket wardrobe workhorse. It offers just enough warmth for a breezy summer evening while looking effortlessly pulled-together. Tuck the front loosely into high-waisted white jeans—a straight or wide-leg cut feels modern and flattering. Crisp white leather sneakers keep the look fresh, clean, and walkable for a full day of island exploring. Layer a thin gold chain necklace and add oversized tortoiseshell sunglasses for a touch of polish. A canvas tote or a woven market basket finishes the outfit with a coastal ease that feels perfectly suited to a morning at the farmers market, a ferry ride, or a casual dinner by the water.
9. Eyelet Midi Dress With Woven Sandals
A white eyelet midi dress embodies the romance of a Nantucket summer. The intricate cutout details add texture and femininity while the cotton fabric keeps things breathable and easy. Look for a silhouette with a defined waist—whether via a smocked bodice, a self-tie belt, or a subtle A-line shape—to create a flattering, timeless drape. Flat woven leather sandals in tan or cognac ground the dress and let the eyelet detailing take center stage. Accessorize with pearl drop earrings for a classic touch and a woven basket bag for that beach-to-dinner versatility. Soft waves in your hair and a swipe of sunscreen complete a look that is equal parts polished and relaxed, perfect for a garden party or a sunset stroll.
10. Polo Shirt With Madras Shorts And Leather Belt
A fitted navy or cream polo shirt tucked into patchwork madras shorts is preppy island dressing at its most authentic. The madras fabric—with its bleeding, mismatched plaid pattern—has deep roots in East Coast summer tradition and brings effortless character to the look. A slim leather belt with a simple brass buckle bridges the two pieces and keeps the silhouette clean. Brown leather sandals or suede driving moccasins finish the outfit without overcomplicating it. For accessories, keep things minimal: small gold knot earrings, a delicate chain bracelet, and classic aviator sunglasses. This outfit feels right at home whether you are grabbing iced coffee in town, browsing antiques, or heading to a casual afternoon cookout by the shore.
11. Shift Dress With Padded Headband And Ballet Flats
A shift dress in a soft pastel—think hydrangea blue, pale pink, or butter yellow—captures the polished femininity that defines so much of Nantucket style. The clean, straight silhouette flatters without clinging, making it a comfortable choice for warm days. A padded satin or grosgrain headband adds that signature old money preppy finish and keeps hair tidy in the island breeze. Simple ballet flats in nude or metallic leather keep the look graceful and walkable on cobblestones. Carry a small structured top-handle bag and add pearl stud earrings for a gentle touch of sophistication. This ensemble works beautifully for a bridal luncheon, a gallery opening, or a day spent exploring the wharf shops with friends.
12. Tweed Jacket With Dark Denim And Riding Boots
When the temperatures dip on a crisp early-autumn Nantucket day, nothing feels more appropriate than a well-cut tweed jacket. Choose a classic herringbone or subtle check pattern in earthy tones like olive, brown, and cream. Layer it over a fine-gauge cashmere crewneck sweater in a neutral shade, then pair with dark-wash straight-leg denim—never distressed, always clean. Tall brown leather riding boots ground the outfit with an equestrian sensibility that fits right into the island’s preppy DNA. A silk scarf tied at the neck adds a refined focal point. This look is ideal for a blustery Bluff walk, a fall visit to Bartlett’s Farm, or a cozy dinner at a shingled inn.
13. White Button-Down Shirt With Linen Trousers And Gold Jewelry
A perfectly pressed white button-down shirt is the ultimate old money building block, and on Nantucket it pairs seamlessly with relaxed linen trousers in sand, cream, or soft navy. Tuck the shirt in fully for a more polished feel, or leave it half-tucked for a laid-back island vibe. Roll the sleeves to just below the elbow—an instant styling trick that makes any button-down look a hundred times more effortless. Slide into flat leather sandals or suede loafers, then layer a few delicate gold chains at the neck. A gold signet ring or a slim watch adds quiet elegance. Throw a woven crossbody bag over your shoulder and you have an outfit that moves effortlessly from a morning meeting to a waterfront lunch.
14. Hydrangea Blue Sweater With White Shorts
The soft blue of Nantucket’s famous hydrangeas has become a color story all its own, and a cotton crewneck sweater in this gentle shade feels like summer on the island. Pull it over a white collared shirt for a preppy layered look, letting the collar and cuffs peek out. Pair with tailored white shorts that hit just above the knee—clean, crisp, and flattering. White canvas sneakers or espadrille flats keep the palette bright and cohesive. A thin gold bracelet and small hoop earrings add just enough polish without taking away from the sweater’s soft charm. This look is perfect for a morning bike ride to Cisco Beach, a casual brunch in town, or an afternoon of island hopping with friends.
15. Quilted Jacket With Straight Jeans And Rain Boots
Nantucket weather can turn quickly, and a quilted jacket in olive green or classic navy is the practical-meets-preppy layer every island wardrobe needs. Its diamond-stitched texture adds visual interest while providing lightweight warmth that doesn’t feel bulky. Wear it over a striped long-sleeve tee and pair with straight-leg medium-wash jeans that look neat but relaxed. Tall Hunter-style rain boots in a dark neutral handle puddle-jumping through town after a summer shower, but they also look intentional and polished when paired with this outfit. A canvas tote and a ribbed knit beanie round out the look for a drizzly day spent ducking into bookstores, cafés, and the Whaling Museum between downpours.
16. Blue Oxford Shirt With Nantucket Reds And Penny Loafers
A light blue Oxford cloth button-down shirt has a soft, textured finish that only gets better with wear, making it a natural partner for faded Nantucket Red pants. The combination of cool blue and warm salmon-pink is unexpected but perfectly balanced, and both pieces carry genuine East Coast heritage. Tuck the Oxford in neatly and add a brown leather belt with a simple brass buckle. Penny loafers in a rich cordovan or cognac leather complete the classic foundation. Keep accessories understated: a slim watch with a leather strap, small pearl earrings, and maybe a tortoiseshell barrette. This is the kind of outfit you wear to a summer cocktail party at the yacht club or a family dinner on the porch.
17. Floral Midi Dress With Straw Hat And Espadrilles
A floral midi dress in vintage-inspired blooms—think small-scale roses, daisies, or hydrangea prints—channels the romantic side of Nantucket dressing. Look for lightweight cotton or crinkle gauze in a flattering wrap or smocked-bodice silhouette that defines the waist gently. A wide-brim straw hat in natural raffia adds sun protection and instant coastal glamour, while flat espadrilles in a coordinating neutral keep the look grounded and comfortable. A straw crossbody bag and delicate gold jewelry maintain the outfit’s lightness. This dress works beautifully for a beachside picnic, a day spent browsing the Bartlett’s Farm market, or an outdoor wedding on the island where you want to look effortlessly feminine.
18. Fisherman Sweater With Denim And Bean Boots
A chunky cream fisherman-style knit sweater—inspired by traditional Guernsey designs—brings texture and warmth to cool Nantucket evenings. The thick ribbed cuffs and collar give it a sturdy, nautical feel that has been part of coastal wardrobes for generations. Pair it with straight-leg medium-wash jeans and classic duck boots that can handle damp grass, sandy paths, and boat decks without missing a beat. The mix of rugged and refined is pure old money practicality. A simple leather watch and stud earrings keep the look clean and unfussy. Toss your hair into a low ponytail and you are ready for a bonfire on the beach, an evening sail, or a walk along Baxter Road as the fog rolls in.
19. White Eyelet Dress With Pearl Earrings And Basket Bag
There is a reason the white eyelet dress shows up in nearly every Nantucket packing list: it is timeless, feminine, and feels inherently celebratory. The broderie anglaise detailing adds just enough texture to keep the all-white palette from falling flat. Choose a midi length with a fit-and-flare shape or a subtle A-line cut for maximum versatility. Pearl drop earrings elevate the look instantly, giving it that inherited-jewelry feel that sits at the heart of old money style. A woven basket bag in natural straw and flat tan sandals complete the outfit with warmth and texture. This is the dress you reach for when you have a bridal shower on the island, a film festival garden party, or a reservation at a waterfront restaurant.
20. Gingham Pants With Oversized Button-Down And Cardigan
Blue gingham pants bring a playful, picnic-ready energy to a Nantucket wardrobe while still feeling classic and pulled-together. Pair them with a crisp white oversized button-down shirt, tucked in loosely at the front for shape. Drape a lightweight mint green or pastel yellow cardigan over your shoulders for that signature preppy layering effect—it doubles as a practical layer when the temperature dips. Flat sandals or white leather sneakers keep the outfit relaxed. A woven basket bag and delicate gold stud earrings tie everything together. This combination is perfect for a Saturday morning at the Nantucket Farmers Market, where you can load that basket bag with fresh-cut flowers, local honey, and sourdough from Bartlett’s Farm.
21. Navy Striped Sundress With Flat Sandals And Sunglasses
A navy and white striped sundress in a breezy A-line or relaxed shift silhouette captures Nantucket style in a single piece. The nautical stripes feel fresh and classic, while the easy fit keeps things comfortable for a full day outdoors. Choose a length that hits around the knee or midi for the most versatility. Slide into flat tan leather sandals—simple, strappy, and walkable. Oversized black or tortoiseshell sunglasses add a dose of old money mystery, and a canvas tote slung over one shoulder carries everything you need for a day at Jetties Beach. A few thin gold bangles catch the sunlight. This is the kind of outfit that looks just as good on a bike as it does at an outdoor café.
22. Cream Cape Coat With Chocolate Trousers And Knee Boots
When autumn arrives on Nantucket and the summer crowds have thinned, layering becomes an art form. A cream cape-style coat in soft wool or cashmere creates a dramatic, elegant silhouette that feels both cozy and refined. Layer it over a thin cream knit sweater for tonal depth, then pair with rich chocolate brown tailored trousers that elongate the leg. Knee-high leather boots in dark brown pull the whole look together with a quiet equestrian confidence. A structured leather tote in tan and vintage-inspired gold earrings add just enough detail. This is the outfit for a late-fall weekend on the island—picture strolling the foggy Sconset bluff walk, then warming up with tea at a shingled café.
23. Silk Scarf At Neck With Blazer And Tailored Shorts
A colorful silk scarf tied neatly at the neck is a small styling detail that changes everything—it brings a vintage polish that feels unmistakably old money. Choose a scarf with a classic pattern like equestrian motifs, tiny florals, or a signature chain print. Tie it in a simple knot or a soft bow at the side of the neck. Let the scarf pop against a navy linen blazer and a simple white tank underneath. Pair with tailored shorts in khaki or sand and flat suede driving mocs. Gold stud earrings and a slim leather watch round out the look. This outfit is ideal for a summer art show, a charity luncheon, or an afternoon spent touring the island’s historic lighthouses.
24. Pastel Lilac Sweater With White Jeans And Raffia Flats
A soft pastel lilac cotton or cashmere sweater brings a gentle, feminine wash of color to a classic white-jeans base. The light purple tone feels fresh and unexpected while still blending beautifully into the island’s soft coastal palette. Wear the sweater tucked in loosely or let it skim the top of high-waisted white straight-leg jeans. Raffia slide sandals in natural tan add texture and a subtle beachy feel without sacrificing polish. A woven clutch or small basket bag, pearl stud earrings, and delicate silver bracelets complete the look. This is a lovely choice for a spring daffodil festival weekend on Nantucket, a casual dinner at a seafood shack, or simply sipping rosé on a friend’s deck as the sun goes down.
25. Striped Button-Down Tied At Waist With Shorts
Take a classic blue-and-white striped cotton button-down and tie it at the waist for an instant dose of casual island charm. This styling trick creates shape, shows a hint of skin, and transforms a traditional piece into something playful and warm-weather ready. Wear it over a simple white camisole or bandeau underneath. Pair with khaki or white tailored shorts that hit mid-thigh for a balanced, flattering silhouette. Flat leather sandals or white sneakers keep the outfit grounded and comfortable. Add a straw fedora, aviator sunglasses, and a canvas tote, and you have a look that feels perfect for a bike ride along the Polpis Road path or a casual afternoon spent popping in and out of the wharf shops.
26. Linen Matching Set With Gold Hoops And Slide Sandals
A coordinated linen set—a relaxed button-down shirt and matching drawstring or elastic-waist trousers in creamy ivory or soft sand—epitomizes the quiet luxury side of Nantucket dressing. The matching pieces create a long, uninterrupted line that reads as intentional and sophisticated, while the breathable linen fabric keeps everything cool and comfortable. Wear the shirt buttoned up or open over a thin white tank. Gold hoop earrings and a stack of thin gold bangles add warmth against the neutral backdrop. Flat leather slide sandals in a coordinating tan shade complete the look. Throw a structured straw bag over your arm and you are ready for an alfresco lunch, a gallery stroll, or an evening of cocktails on a harbor-facing patio.
27. Tennis Dress With White Sneakers And Visor
With pickleball courts and tennis clubs woven into Nantucket’s social fabric, a sporty-chic tennis dress is a completely acceptable—even expected—part of the island wardrobe. Choose a white or pale blue tennis dress with built-in shorts and a flattering racerback or cap-sleeve silhouette. Crisp white leather sneakers keep the look clean and athletic. A white visor shields the sun while adding a preppy finish that nods to the country club set without feeling try-hard. A simple fitness watch and small stud earrings are all the jewelry you need. Toss a lightweight crewneck sweater over your shoulders for that post-match cool-down walk, and you are ready for courtside coffee or a casual lunch at the clubhouse.
28. Cream Knit Top With Tailored Trousers And Structured Bag
A fine-gauge cream knit top—whether a sleeveless shell, a cap-sleeve cashmere tee, or a lightweight merino crewneck—is one of the hardest-working pieces in any old money wardrobe. Tuck it into a pair of tailored trousers in warm beige or soft navy for a look that is simple, elegant, and effortlessly pulled together. The trousers should have a clean, straight-leg cut with front pleats or a flat front for that tailored finish. Slip into nude suede loafers or low-block-heel sandals. A structured leather top-handle bag in tan or black anchors the softness of the knit. Add a slim gold watch and delicate chain earrings. This outfit transitions beautifully from a work meeting to a dinner reservation at The Nautilus.
29. Boatneck Cotton Sweater With Cropped Chinos And Espadrilles
A boatneck sweater in crisp white or navy blue is inherently nautical, its wide neckline originally designed to accommodate the movement of sailors. Today, it brings a subtle maritime reference to an otherwise simple outfit. Pair it with cropped chinos that hit just above the ankle, showing off flat espadrille sandals in natural canvas and jute. The slightly cropped pant length keeps the look light and summery. A thin braided leather belt adds texture at the waist. Small gold knot earrings and a simple chain bracelet provide polish without distraction. A woven crossbody bag completes the ensemble. This outfit feels right at home whether you are walking the docks at Straight Wharf or enjoying a casual lunch at a harborside restaurant.
30. Nantucket Reds With Navy Polo And Braided Leather Belt
We end where every Nantucket style conversation eventually lands: on the island’s most iconic garment. Faded Nantucket Red pants—now softened to that perfect dusty salmon shade—paired with a classic navy polo shirt create an outfit that is pure, distilled East Coast old money. The polo should be fitted but not tight, with a clean collar and no visible logos. A braided leather belt bridges the red and navy seamlessly, and brown leather boat shoes or penny loafers complete the timeless base. Add a simple watch with a leather strap, small pearl studs, and a canvas belt bag or crossbody for practicality. This is the outfit you wear when you want to look like you have been summering here for generations—because it genuinely captures that spirit.
Conclusion:
Nantucket old money style is less about what you buy and more about how you wear it. The faded reds, sun-bleached linens, and well-loved cable knits tell a story of summers accumulated over years, not trends chased in a single season. The beauty of this aesthetic lies in its restraint: neutral palettes, natural fabrics, and silhouettes that never scream for attention. You do not need a house on the bluff or a dinghy at the wharf to channel it. Start with one or two of these head-to-toe outfits, focus on fit and fabric quality, and build slowly. Before long, your wardrobe will feel as timeless and effortless as a Nantucket afternoon—and that quiet confidence is exactly what old money dressing is all about.
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