Everything I Wore in the Hamptons

Everything I Wore in the Hamptons
📍 Westhampton Beach, NY

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Sweater Vest || Jeans || Sandals || Handbag || Earrings

There’s something about the Hamptons that brings out the best in my summer wardrobe. Equal parts polished and effortless, the style here leans coastal, classic, and just the right amount of dressed-up. For this trip, I packed pieces that felt true to that spirit, think breezy linens, tailored separates, and a few playful details for brunches, vineyard walks, and afternoons in town. Whether we were having coffee on the porch, strolling through Sag Harbor, or dressing up for brunch, each outfit was intentionally pulled together, but never overthought. Below, I’m sharing everything I wore over our few days Out East. Here are eight looks that felt equal parts functional and refined, with that timeless Hamptons ease.

Dress || Sandals || Handbag || Earrings

Drive to Southampton

This may be a hot take, but I usually prefer to travel in midi or maxi dresses. That’s especially true for road trips! It gives me a chance to move around more freely. While making the early morning drive from Connecticut to the Hamptons, I opted for this Hill House Home Nap Dress. The Mariner print is part of one of their more recent summer collections and is perfectly nautical for a New England summer. Wearing a dress like this also ensures that I’m ready for lunch and cocktails as soon as we arrive!

Button-Down Shirt || Sweater || Pants || Sandals || Tote Bag || Earrings

Southampton Coffee Run

Early morning trip to Golden Pear Cafe, but with a Coastal Grandmother aesthetic. Our summer days in the Hamptons felt unseasonably cool to start, but were usually quick to warm up. Because of that, I needed to dress in some layers. A sleeveless button-down shirt from J. Crew Factory pair perfectly with a classic La Ligne striped sweater and white linen pants from J. Crew. The head-to-tie white with a pop of color via the draped sweater may become a staple all season long.

Button-Down || Skirt || Similar Flats || Hat || Tote Bag || Earrings

Lunch in Amagansett

It was a breezy day in Amagansett, to the point my straw hat nearly blew away several times, and I was thankful for wearing layers. Something about this outfit felt peak Nancy Meyers. One thing is for certain, it forever put the Hill House Home Delphine Skirt in my list of favorites. So comfortable and, with the smocked waisted band, it was surprisingly flattering! The green loafers were a spontaneous purchase from the local Sabah boutique. I’m usually not the biggest shopper when I’m on vacation, but the unique color really called my name and I’ve been wearing them consistently ever since!

Dress || Sweater || Flats || Tote Bag || Earrings

Grabbing Donuts in Westhampton Beach

Since we were traveling with our little one, we would sneak away from the house bright and early to keep things quiet for our friends. This gave us ample time to drive around, explore some stunning neighborhoods, and pick up some sweet treats. One of our early mornings brought us to Westhampton Beach. I genuinely love the little downtown here. We grabbed coffee from One Trick Pony, highly recommend, and grabbed donuts from Beach Bakery to bring back to the house. Admittedly, I was a little overdressed for a donut run, but I love the pairing of this white linen dress from J. Crew and red cardigan from Sézane all the same.

Sweater || Jeans || Sandals || Similar Hat || Tote Bag || Earrings

Brunch at Canoe Place Inn

Consider this my official summer uniform for 2025. The cooler temperatures this year has me reaching for my cozy sweaters over and over again. What’s my absolute favorite on the roster? It’s hands down this cropped American flag sweater. I bought it from Tuckernuck last year and I’ve found myself wearing with each passing season. Paired with cream wide leg jeans, it create a monochromatic outfit that’s effortless and timeless. I honestly couldn’t think of a better look for brunching at the historic Canoe Place Inn.

Dress || Sandals || Tote Bag || Earrings

Exploring Sag Harbor

Our final stop during our Hamptons tour was for brunch and some exploring in Sag Harbor. A major whaling port in the 19th century, this town has such a colonial charm to it. We started with breakfast at Baron’s Cove. Their restaurant patio offers amazing views of the harbor and was a great place to linger over brunch and bellinis. This Tuckernuck maxi dress was made for strolling through the downtown. Although it was fairly crowded on the summer weekend, we made the most of it by popping in and out of boutiques and extending our walk to be among the historic homes. On our next visit, I hope to get a dinner reservation at the American Hotel.

Sweater Vest || Button-Down Shirt || Sweater || Jeans || Sandals || Handbag || Earrings

Looking back, I’m really happy with the balance I struck: neutral staples mixed with a few statement pieces, all easy to rewear and restyle. These eight outfits carried me through everything from casual mornings to more polished outings, without ever sacrificing comfort. If you’re heading to the Hamptons, or planning any summer getaway that calls for relaxed, elevated style, I hope this round-up gives you a bit of inspiration. And if you’re wondering what I’d pack again? Definitely the American flag sweater, my go-to basket tote bag, and that seersucker maxi. They were the unsung heroes of the trip.

Love from the Hamptons,
Katie

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