What to Pack for Nantucket
April 24, 2026
We’re all about helping you look your best, wherever you are in the world. Here’s what to pack for a trip to Nantucket, according to Maddy Grayson and Cynthia Cook Smith.
Meet Our Experts: Maddy Grayson and Cynthia Cook Smith
As Tuckernuck’s co-founder and a life-long seasonal islander, Maddy considers Nantucket her second home. After 30+ summers spent on Nantucket, she knows the island (and its style) like the back of her hand.
Cynthia, a former editor at Vogue and stylist, is a contributing fashion editor for Tuckernuck. Cynthia and Maddy connected over their lifelong love of Nantucket and their shared experiences as seasonal islanders.
Here’s what they would wear to fish, hike, and spend quality time with friends and family.
Nantucket Style, Explained
The Signature Look: At its core, Nantucket style is relaxed, refined, and layered. It’s never about labels or trying too hard. It’s the place where families return season after season, generation after generation. The historic whaling town’s style is rooted in the island’s active lifestyle, unpredictable weather, and the belief that clothes (like the island) get better with age.
Our Fashion Fundamentals: Striped tees, swim, chinos, and cotton sweaters are island essentials.
What to Pack for Nantucket
With 37 pieces you’ll wear throughout your stay, we’ve got everything you need organized by category.
DRESSES
Mini dress
Sundress
White dress
Dinner dress
TOPS
Striped tee
Button down
Poplin tank
Evening top
LAYERS
Cardigan
Cotton pullover
Windbreaker
Barn jacket
BOTTOMS
Chino shorts
Tailored shorts
White denim
Linen pants
Maxi skirt
Cocktail pants
SPORT
Polo
Sport tank
Athletic shorts
Tennis skirt
Leggings
SWIM
One piece
Bikini
Coverup
FOOTWEAR
Boat shoes
Canvas sneakers
Flat sandals
Espadrilles
ACCESSORIES
Costume jewelry
Silk scarf
Sunglasses
Sun hat/baseball cap
Monogrammed boat bag
Raffia clutch
Crossbody bag
Our Top 5 Packing Tips
Layer Up
Pack a cotton sweater (or two) for New England weather.
Keep It Natural
Think raffia and bamboo accents, not patent leather and luxury leather.
Bring Sportswear
With fishing, golfing, and hiking, you’ll want activewear options.
Dress Up for Dinner
Have a cocktail dress on hand for dinner dates and nights out.
Lose Your Heels
Canvas espadrilles, flats, and sneakers are best for cobblestones, docks, and sand.
Let us help you dress like a local.
Beach
Dive right in with a one piece in a playful madras print or stripes. Have a pair of white linen pants and a cotton sweater in your beach bag to throw on after your swim.
Bike
Ride in style in a polo, wide-leg chinos, sunnies, and canvas sneakers. Finish the look with a bucket hat.
Brewery
Wear a cute, easy sundress for lunch at Cisco. Keep your accessories classic in Jacks and tortoiseshell frames.
Boat
Don’t miss the boat! For a trip to Tuckernuck island, wear an easy tee or one piece, shorts, and a cotton sweater over your shoulders. Cynthia’s tip: bring a pair of sweatpants to change into for the ride home.
Bites
For a more formal dinner at Chanticleer, put on a cocktail dress in a fresh color and finish the look with canvas espadrilles, a raffia bag, and a silk scarf. For a more casual dinner, throw on a madras skirt and a black tank.
FAQs
Why do we love Nantucket?
Tuckernuck co-founders Maddy and Jocelyn spend their summers in Nantucket, and their favorite island off Nantucket, Tuckernuck, is our brand’s namesake. Over the years, we’ve collaborated with Murray’s Toggery for our Tuckernuck x Nantucket Reds™ collection, and we are opening a store on Nantucket this summer!
What is the weather like on Nantucket?
In the summer months, temperatures range from highs in the upper 60s and 70s to lows in the 50s, with the mornings and evenings tending to be a bit cooler. As Maddy says, the weather can change within an hour, so make sure to carry a sweater while you’re out and about.
What to pack for guys visiting Nantucket?
For the guys, keep it simple. Stick to polos, button downs, khakis, and Nantucket Reds™. If he left something at home, stop in to Murray's Toggery, the home of Nantucket Reds™, on Main Street.
What are three things I have to pack for a trip to Nantucket?
Maddy’s non-negotiables: athletic clothes, a nice dress for a night out, and a trusty layer. Everyone’s active in exercise clothes during the day, but things slow down come dinnertime. You’ll want to make sure to dress the part.
What shouldn’t I wear during my trip to Nantucket?
Don’t wear heels! With cobblestone streets, opt for a cute pair of espadrilles or flats. Cynthia recommends canvas shoes as they are easy to clean and dry quickly if they get wet.
Get Inspired:
#Tuckernucking on Nantucket