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Mytheresa big sale, checked October 27: The Nour Hammour brown suede Barn jacket in this edit is in the extra 20% off sale offer on eligible orders of $350 or more, through November 8 at 11:59 p.m. CET (2:59 p.m. Pacific). Exclusions apply; check the retailer’s terms before buying. Other picks are not presented as part of this offer.
The Hamptons in winter are a different trip from the beach-weekend version. I would go for a museum afternoon, a village walk, a prepared dinner to take back to the house and a few small shops, not a packed social calendar. The clothes should follow that slower plan: a cream cropped jacket, a brown Chelsea boot, a dark-green knit, a scarf you actually want to wear.
Jenni Kayne Cashmere Amelia Crewneck in Warm Sand
The Warm Sand Amelia crewneck is knit from 100% chainette cashmere, with an oversized straight body. The textured knit is an easy village layer with your own straight jeans or wool trousers. Wear it beneath the coat that suits the forecast, then repeat it for a quiet dinner instead of packing a second outfit. Jenni Kayne Cashmere Amelia Crewneck in Warm Sand. Another option in the same family is the Jenni Kayne Flynn cashmere crewneck in black.
Hamptons in Winter: Choose One Village as a Base
East Hampton works for a Guild Hall afternoon and a little village browsing. A Water Mill art day belongs with the Parrish Art Museum, with time for lunch nearby. Sag Harbor is another good direction if the home and gift shops interest you most. Pick one base and one outing, leaving the rest of the weekend for whatever you find along the way.
Winter changes the rhythm: some favorite summer shops close for the season, holiday hours matter, and a quiet Monday can feel very different from a Saturday. Build in an indoor option instead of expecting a long windy beach walk to carry the whole afternoon.
Put a short village walk on either side of the visit. Obligato at 47 Main Street is the independent clothing-boutique option to check, with a mix of women’s pieces from smaller designers and established brands. Carissa’s Pantigo cafe and bakery at 221 Pantigo Road is the coffee-and-lunch direction when it is open. A winter outing feels better with a warm place to pause than with five hurried stops.
Photo credit: Polo Ralph Lauren
Photo credit: Aquazzura
Photo credit: Ganni
Photo credit: Ralph Lauren Collection
For a dry village walk and coffee at Carissa’s, wear the cream Polo Ralph Lauren teddy-collar blouson with your own jeans and a warm knit. The Aquazzura Gaspard espresso-suede Chelsea boots keep the lower half simple. Add the Tiramisu leather crossbody for hands-free browsing, and use your own weather-ready coat and footwear when the conditions need more than this outfit.
Polo Ralph Lauren Cream Cropped Zip-Front Jacket with Teddy Collar
The cream blouson keeps a jeans-and-knit outfit light without turning it into a summer look. It has a detachable teddy collar, elasticated cuffs and a zip front, with the small embroidered Pony at the chest. The shell is polyester, not shearling. Wear it for the weather it can handle, and add your own warmer coat when a winter forecast calls for one. Polo Ralph Lauren Cream Cropped Zip-Front Jacket with Teddy Collar.
Aquazzura Gaspard Espresso-Suede Chelsea Boots with Braided Trim
These brown Chelsea boots have a round toe, elasticated side panels and braided leather trim. The upper is goat suede, with a leather lining and rubber sole. They make a polished dry-day alternative to a heeled boot. A rubber sole does not make suede waterproof or guarantee grip on ice; bring weather-ready shoes for wet or icy conditions. Aquazzura Gaspard Espresso-Suede Chelsea Boots with Braided Trim.
An East Hampton Art Afternoon at Guild Hall
Guild Hall is at 158 Main Street in East Hampton. Its galleries, performance program and coffee bar make it a useful indoor anchor. Read the current calendar before choosing your weekend; gallery exhibitions and performances have their own dates.
For Guild Hall and dinner afterward, pair the Ralph Lauren Collection cream off-the-shoulder cashmere sweater with your own wool trousers and dinner shoes. The burgundy Ganni Bou Small top-handle bag brings one dark accent beside the cable knit. Wear a warm coat outdoors and save the bare neckline for the heated indoor part of the evening.
Burgundy glossy-textured Bou Small bag by Ganni
For the Guild Hall afternoon and dinner afterward, the Ganni Bou Small bag in burgundy adds a dark, glossy accent to the cream knit and brown boots. The textured fabric and braided handle give it a different finish from the pebbled crossbody below. Pick the small top-handle shape for a shorter outing rather than expecting a roomy day tote.
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Ralph Lauren Collection Lux-Cream Cable-Knit Off-the-Shoulder Cashmere Sweater
The cream cable-knit sweater is the fitted dinner layer, with a foldover off-the-shoulder neckline and long sleeves. Wear it with straight trousers and your own dinner shoes indoors, then add your coat for the trip there. Cashmere and the rib-knit trim keep the texture soft without needing another pattern. Ralph Lauren Collection Lux-Cream Cable-Knit Off-the-Shoulder Cashmere Sweater.
A Water Mill Museum Day and a Sag Harbor Detour
The Parrish Art Museum is at 279 Montauk Highway in Water Mill. Make it the main event of that day: see the current exhibitions, leave time for the museum shop and check the cafe arrangements. The museum lists regular opening days from Thursday through Monday, with Tuesday and Wednesday closures and additional holiday closures.
For a separate Sag Harbor afternoon, Comerford Collection at 83 Main Street is a home-and-design stop, and Sage & Madison at 31 Madison Street is a boutique and gift-shopping option. It is a nice way to find something for the house or a host, rather than spend the day doing the same shopping you could do anywhere.
Photo credit: Zimmermann
Photo credit: Loewe
Photo credit: Ulla Johnson
Photo credit: Tory Burch
Photo credit: Quince
Photo credit: Ruslan Baginskiy
Photo credit: Nour Hammour
For the Parrish museum and a separate Sag Harbor shopping afternoon, choose the Zimmermann Valiant Palomino shearling jacket over your own simple knit and trousers. The Loewe Light Beige fringed cashmere scarf keeps the palette quiet. Carry the warm-brown Romy crossbody and wear the espresso suede boots only for a dry route; choose your own weather-ready shoes when needed.
Zimmermann Valiant Palomino Shearling Jacket with Leather Belt
The Valiant jacket is the special piece here. Plush brown shearling, notched lapels and a leather belt give it shape over a quiet knit and trousers. Keep the rest of the outfit simple so the jacket stays the point. It needs specialist cleaning, and the generous shape is worth checking against your measurements before ordering. Zimmermann Valiant Palomino Shearling Jacket with Leather Belt.
Light Beige fringed cashmere scarf by Loewe
The Loewe Light Beige fringed cashmere scarf is the quieter finishing piece for a village walk. It is 100% cashmere, with fringed ends. Wear it with the brown shearling jacket and straight trousers, or with your own warm coat when the forecast calls for one. Choose this scarf for the long, fringed shape; the oatmeal wrap below is the shawl-like alternative, not another layer you need to pack.
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Prepared Food for a Quiet Night In
Loaves & Fishes Foodstore at 50 Sagg Main Road in Sagaponack says it is open year-round. Browse the current prepared-food menu and take home a dinner that suits the people at your table. A good takeaway meal means you can spend the afternoon out instead of turning a two-night escape into a full grocery-and-cooking project.
Round Swamp Farm’s Famous Chicken Salad and baked goods are worth a stop when its markets are open.
For a Loaves & Fishes stop, wear the Ulla Johnson Lila Militaire-green merino pullover with your own high-waisted jeans or trousers. Add the Tory Burch Romy Soft Crossbody in Tiramisu so your hands are free for the food bags. The cream teddy-collar jacket is the lighter outer layer; bring the winter coat you need for the actual forecast.
Ulla Johnson Lila Militaire-Green Waffle-Knit Merino Pullover with Sailor Collar
The Lila pullover has a textured waffle stitch, sailor collar and puff sleeves with rib-knit cuffs. Its cropped length works with higher-waisted trousers, while the deep green brings color beside the cream jacket and brown boots. Pure merino wool makes this a useful village layer beneath a warmer coat. Ulla Johnson Lila Militaire-Green Waffle-Knit Merino Pullover with Sailor Collar.
Tory Burch Romy Soft Crossbody Bag in Tiramisu
The small Tiramisu Romy crossbody brings a warm brown accent to the cream jacket and green knit. Pebbled leather, a zip top and an adjustable strap make it a useful option for village browsing and dinner. Check the dimensions against your own essentials before making it your only bag for the weekend. Tory Burch Romy Soft Crossbody Bag in Tiramisu.
What to Wear in the Hamptons in Winter
Use your own straight jeans or wool trousers as the base, then choose one jacket and one useful knit. The edit below mixes softer layers with the pieces that make an ordinary outfit feel considered. A shearling jacket is the statement choice; a cream blouson is a different, lighter direction. They are alternatives, not a reason to pack both. Bring your real cold-weather coat if the forecast needs it.
Quince Mongolian Cashmere Wrap in Oatmeal
Oatmeal keeps the soft neutral palette beside the brown jacket and boots. This generous 100% Grade-A cashmere wrap can be worn as a scarf outdoors or draped as a shawl indoors; it is not a narrow fringed scarf. Pack it as an extra layer for a museum afternoon or dinner, not as a substitute for a real winter coat. Quince Mongolian Cashmere Wrap in Oatmeal.
The Hamptons in Winter Packing List
Pack two useful bottoms, a plain tee or long-sleeve base, one knit, the jacket that suits the forecast and a real warm coat if you need it. Bring familiar walking shoes plus weather-ready footwear, socks, gloves, a scarf, underwear, sleepwear and one small bag. For dinner, repeat the trousers and change the top rather than packing a separate outfit for every meal. Add medicines, chargers, toiletries, sunscreen and a compact umbrella. If you are bringing prepared food back to the house, bring a cooler and keep it chilled. For the bathroom bag, I always bring disposable face towels. One side is soft and smooth and the other is lightly exfoliating, so they are great after washing your face for drying it and making sure all your makeup is off without dirtying a towel. Towels harbor bacteria if they are not washed daily, and a body towel should not go on your face. They are ideal for travel so you are not using hotel towels on your face. I use them all the time.
A winter weekend is a good excuse to do less: one museum, a small-shop afternoon, a walk if the weather allows and dinner somewhere warm.
More Weekend Plans and Outfits
Read my Hamptons small-shop and food weekend guide for the village-shopping version. For a country escape, see my Hudson Valley fall and winter weekend guide. For colder mountain plans, browse my ski-trip packing edit.
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