POSTCARD FROM…Sag Harbor, Long Island, NY

Habitually Chic founder Heather Clawson shares her annual trip to the most low-key village in the Hamptons

By Heather Clawson

HELLO FROM…Sag Harbor

WHERE I’M STAYING…I’ve been staying at Baron’s Cove every year since they opened in 2015. The best thing about Sag Harbor is that it’s a year-round town, so most places don’t close at the end of the season like other spots in the Hamptons and Long Island. I love to come out in June before high season starts and the weather is temperate. I also enjoy visiting in late October or early November when the leaves have changed for a picturesque fall weekend getaway.

Left: Baron’s Cove; Right: The windmill on Long Wharf

WHAT I PACKED…You don’t need to pack high fashion for Sag Harbor. It’s a casual harbor town where preppy fashions are your best bet. In addition to midi dresses and sandals from Tuckernuck, I always pack chunky cotton sweaters and white jeans from J.Crew for cooler nights on the water. I stick to shades of navy, pale blue, and white with pops of salmon pink or yellow.

THE BEST MEAL I HAD…I always meet my friends in town for a meal at The American Hotel, but I also love the Cajun chicken at Le Bilboquet. This trip, we had a great dinner at the newly opened El Tacobar from Laurent Tourondel on Main Street. Everyone should get ice cream at Big Olaf’s and walk down to the end of Long Wharf to ogle the yachts and watch boats coming and going. If I want to grab take out for the beach or the Jitney ride home, I go to Harbor Market for their turkey sandwiches. Grab a drink at Baron’s Cove and listen to some live music and maybe you will be rewarded with an epic sunset that turns the entire sky shades of orange and red.

Left: Bloom; Right: Main Street

MOST FUN THING I DID…I love to take a long walk down Main Street to Canio’s Books and photograph all the charming houses along the way. Then I walk back through town to shop at all my favorite stores. Sag Harbor has some very sophisticated boutiques like Ryland and Bloom, who both bring back treasures from France, but also an old-school five-and-dime, Sag Harbor Variety, where you can find anything you forgot and fun holiday decorations. You never know what you might find at Sage Street Antiques, but make sure you go on Saturday when both stores are open. I always keep my eyes peeled for classic cars cruising around town, too.

PLAYLIST ON REPEAT…I create Spotify playlists for each season and some trips. I made a mellow Summer 2023 playlist that I listened to on the way out to Sag Harbor on the Jitney.

THE BOOK I READ (AND WOULD RECOMMEND)…I always go to Sag Harbor Books and look to see what’s new—I love to read all the employee recommendations and choose what sounds most intriguing. It’s fun to scope out all the first editions in the back, too.

Local homes in Sag Harbor

A THING OR TWO I LEARNED…Sag Harbor was founded between 1707 and 1730 was once one of the largest whaling ports in the United States. After the Second Session of Congress on July 31, 1789, Sag Harbor was declared as the first official port of entry to the United States. As the first stop for ships entering United States territory, Sag Harbor received ships bound for New York City. The United States government placed a customs house in the town, the first on Long Island, to collect duties and other fees. You can learn more at the Sag Harbor Whaling and Historical Museum and Custom House in town.

THE BEST THING I’M BRINGING HOME…Molecule 01 by Escentric Molecules perfume from Bloom, oatmeal cookies from Harbor Market, and small treasures from Sage Street Antiques.

Heather Clawson is the founder of the lifestyle site Habitually Chic, where she has covered fashion, design, art, architecture, films, travel, and more, since 2007.