Hamptons Weekend: Small Shops, Chicken Salad and What to Wear

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Polo Ralph Lauren Brown Cable-Knit Wool-and-Cashmere Cardigan

Brown cable knit is the easy first layer for a village morning. This cardigan is wool with cashmere, with the small Pony embroidery at the chest. Wear it buttoned with your own straight jeans and a flat shoe, then bring it along over a dress when lunch runs into the afternoon. Polo Ralph Lauren Brown Cable-Knit Wool-and-Cashmere Cardigan.

A Hamptons weekend is more interesting when the plan leaves room for the little shops, a good prepared-food counter and a long lunch. East Hampton is a lovely base for this version: one village morning, one stop for something delicious to take home, and clothes that work for both. Think brown cable knit, woven suede loafers, a printed shirtdress and a soft-blue sweater. The mood is polished, but nobody needs a suitcase full of occasion outfits.

Altuzarra Claudia Hunter-Green Scarf-Print Midi Shirtdress

Claudia gives the weekend one dress that feels dressed without needing a complicated outfit. The Hunter Diamond print, spread collar, long sleeves and buttoned front keep it sharp; the defined waist changes the line from a loose cover-up. It is viscose and dry-clean only. Add a quiet brown shoe and let the print do the work. Altuzarra Claudia Hunter-Green Scarf-Print Midi Shirtdress.

A Hamptons Weekend in East Hampton: Small Shops First

Start with Obligato at 47 Main Street, an independent East Hampton boutique that has been there since 1985. It carries women’s clothing from independent designers and established brands, with the kind of personal attention that makes browsing feel different from clicking through a huge catalog. Give yourself time to try something outside your usual uniform.

For coffee and a bakery stop, Carissa’s Pantigo location is at 221 Pantigo Road. It combines a cafe, bakery, pantry and bar. Check its current opening days before setting out; a weekend plan should not depend on an old weekday schedule. Keep this part of the day in East Hampton rather than adding every village to one rushed loop.

Bottega Veneta Silenzio Dark-Caramel Woven-Suede Loafers

The woven suede is the detail that makes these loafers feel special even with a plain cardigan. Silenzio has a round toe, leather lining and a leather sole. They are a dry-day choice for browsing and lunch, not rain shoes. Try a new pair at home before asking them to carry a full shopping day. Bottega Veneta Silenzio Dark-Caramel Woven-Suede Loafers.

Round Swamp Farm: The Chicken Salad Stop

The prepared-food stop is Round Swamp Farm, not Roundtree. Its East Hampton market is at 184 Three Mile Harbor Road. The menu includes its Famous Chicken Salad, curry chicken salad, fresh lobster salad, baked goods and plenty of other picnic possibilities. I would pick one salad, bread and something sweet, then let lunch be the simple part of the day.

What is in the case changes with the season. Round Swamp’s own pages currently show different opening-day schedules, so check directly before making a special trip, especially in the colder months. Buy for the meal you actually have planned and keep chilled foods cold on the way home. The appeal is the ready-made lunch, not a reason to overbuy.

Tory Burch Small Fleming Suede Carryall in Toffee

Toffee suede brings the small bag into the cooler-weather wardrobe. The Small Fleming Carryall has napa trim, a top handle and a convertible chain shoulder strap, with a magnetic snap closure. Its compact shape works beside the printed dress or brown cable cardigan. Check the dimensions against your own essentials before choosing it as your only bag for the weekend. Tory Burch Small Fleming Suede Carryall in Toffee.

A Foodstore Detour in Sagaponack

For a separate Sagaponack stop, Loaves & Fishes Foodstore is at 50 Sagg Main Road. It serves freshly prepared takeaway food and says it is open year-round. This is the foodstore to put on the current itinerary, rather than planning a visit to the old Barefoot Contessa shop. Browse the day’s menu and choose what looks good for your own table; do not count on one dish always being available.

Independent Home and Gift Shops Worth a Detour

Comerford Collection has a Bridgehampton shop at 2442 Main Street and a Sag Harbor shop at 83 Main Street. It is the home-and-design stop for furniture, lighting and objects, rather than another rail of clothes. If you are spending the afternoon in Sag Harbor, pair the Main Street location with Sage & Madison at 31 Madison Street, whose boutique and gift baskets make it a thoughtful stop when you are staying with friends.

Khaite Annette Espresso Merino-Wool Turtleneck Sweater

Annette is the rich espresso knit for a cooler day. Pure merino wool, a relaxed shape and a soft high neckline give it a clean line over jeans or tailored trousers. I would keep everything around it simple: small earrings, a brown bag and one good shoe. Follow the dry-clean care instructions rather than treating it like a casual wash-and-wear sweatshirt. Khaite Annette Espresso Merino-Wool Turtleneck Sweater.

Choose East Hampton for the first morning and one other village for the second, instead of trying to do all the shops in a day. Check individual opening days and seasonal hours before driving over. These are reasons to browse in person, not a list of chain stores you could find at home.

What to Wear for a Hamptons Weekend

The shopping edit is built around warm brown, soft blue and prints with a little character. The knits and loafers are for a dry village day; the dresses and smaller bag are for lunch or dinner. Add your own jeans, a plain tee and familiar walking shoes. In rain, change the suede for a pair that can take the weather. A good weekend outfit is one you can repeat with a different layer.

Quince Mongolian Cashmere Boxy Crewneck in Faded Denim

Faded Denim softens all the brown in the suitcase. This 100% Grade-A Mongolian cashmere crewneck has a boxy fit, drop shoulders, a split hem and rolled-edge details. Wear it with your own cream trousers or denim, then repeat it for the second village morning. Hand wash cold and lay it flat to dry. Quince Mongolian Cashmere Boxy Crewneck in Faded Denim.

Jenni Kayne Leather Camilla Mule in Chocolate

Chocolate leather keeps the dinner shoe quiet beside either printed dress. Camilla is an open-toe, fisherman-inspired slide in soft folded leather, not a suede heeled mule. Keep it for dry weather and indoor plans, and try the fit at home before packing. Bring familiar walking shoes for a longer village day rather than expecting one new slide to do everything. Jenni Kayne Leather Camilla Mule in Chocolate.

Polo Ralph Lauren Brown-and-Blue Plaid Cotton-Twill Shirtdress

For a more casual dress day, this cotton-twill shirtdress brings a straight-point collar, buttoned cuffs, side pockets and brown-and-blue plaid. Wear it with loafers for the village and add the cable cardigan as the day cools. It is an alternative to the other dresses, not another outfit you have to pack on a two-night trip. Polo Ralph Lauren Brown-and-Blue Plaid Cotton-Twill Shirtdress.

The Hamptons Weekend Packing List

Pack one pair of jeans or trousers, two tops, one useful knit and one dress that suits your dinner plans. Bring the dry-day shoe you already know, a rain-ready alternative if the forecast calls for it, underwear, sleepwear and a coat for the actual temperature. A crossbody bag for daytime and a small evening bag are enough. Add sunscreen, toiletries, medicines, chargers and a compact umbrella. If food shopping is part of the trip, leave space in the car for a cooler rather than squeezing everything into the clothing bag.

Keep the first morning for East Hampton and the second for the village you most want to browse. If it is a winter trip, check seasonal openings before you book the rest of your day. The same cardigan and shoes can work for both mornings; nobody needs a fresh outfit for every stop.

A Pale Gray Polo Sweater

For a village walk or a cozy lunch, the Jenni Kayne Burke alpaca polo sweater in Pale Gray is a soft neutral layer. Check the fiber content and care instructions on the listing.

More Weekend Outfit Ideas

For a different kind of country weekend, read my Hudson Valley fall and winter weekend guide. For another complete suitcase, see my Mexico wedding-weekend outfit and packing guide.

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