What the Women of Nantucket Are Wearing

Hill House

This may become the new Lilly Pulitzer. It’s guaranteed that if you spend just 30 minutes walking through town and people-watching, you will see at least three dresses by Hill House. Their iconic dresses have a smocked top with a flare midi skirt. However, I’ve recently been intrigued by their new popular style of the Ezra Dress. This is a more fitted bodice with a similar flare midi skirt, and it comes in multiple beautiful summer floral patterns.

The Hill House storefront on Main Street

Staud

Every single young woman has a Tommy bag or a dupe of the Tommy bag. You can spot them at a range of places, from Cisco Brewers during the day to the Brant Point Grill restaurant in the White Elephant at night. The great thing about their storefront in Nantucket is that they also carry the limited-edition Nantucket Tommy bags. The 2025 drop features an array of sailboats on the front and Brant Point Lighthouse on the back, on a bright teal background. The 2026 drop features a map of the island, including small callouts with the names of the island’s regions on the front, and a large blue whale on the back, on a navy blue background.

The limited-edition 2025 Nantucket Tommy bag in the Staud storefront

Zimmerman

I’m trying not to be biased because this brand is me if I could wear one clothing brand for the rest of my life, but it is true, you can find Zimmerman silhouettes throughout the island! You can always identify a Zimmerman through the quality of the fabric, typically very structured linen. If it’s not Zimmerman that I am seeing, then I’m seeing dresses that were inspired by them.

Chanel

Chanel flats are the go-to. This makes sense when you think of the difficult cobblestone streets and brick sidewalks and realize that flats are much more functional than heels on island. Tweed jackets are a popular fixture for when the temperature drops at night and your sunburn isn’t radiating heat anymore while standing in line for the Juice Bar after dinner.

Tommy bags are sold in many boutiques here like Erica Wilson, not just Staud!

Doen

Nantucket is a unique town in that chain businesses are not allowed to open a storefront in the historic town district. One of the only exceptions to this is Ralph Lauren, which has had a storefront on Main Street for as long as I can remember, so it’s “grandfathered in.” When I first saw the new Doen store in town, I thought they violated this rule because I am very familiar with the brand due to its recent surge in popularity. However, this is only their seventh storefront! It is worth a visit to Doen while on island as they capture the bohemian beach aesthetic perfectly.

Sometimes I find myself changing out of an outfit because it feels too “NYC” or not “Nantucket” enough. At the end of the day, as long as you wear something you feel good in and are confident about it, you can wear anything. I’ve seen outfits at the Chicken Box ranging from two-piece sequin sets for over $900 all the way to jeans and a sweater. Come with your best outfits! And that means something different for everyone. Nantucket tends to be a more formal-leaning place in terms of dressiness, and the brick sidewalks are basically fashion runways, so come as you please and enjoy your time in Lilly Pulitzer or Vineyard Vines.

For more inspiration and insider recommendations, visit our Nantucket page.