Martha's Vineyard Has an Unspoken Dress Code—Here's What a Local Recommends Wearing, From $14

Travel + Leisure

2 days ago

The coastal island of Martha's Vineyard, Massachusetts, has always been an attractive summer retreat. Pastel-colored gingerbread cottages, windswept dunes, and oak-lined streets without traffic make it a whimsical destination. For Erin Goldson, who is now based in New York City but whose family history on the island dates back four generations, the island is much more than just a summer vacation.
'The Vineyard is home. My great-grandmother was the first in my family to buy a home on the island, and my family has been coming ever since,' she says, noting that her parents met on the island, and it is where her late father is buried, as it was his happy place. 'My 98-year-old grandmother still lives there year-round,' she adds.
As a lifetime Vineyarder, Goldson is always in the know with social events, community efforts, and simple pleasures like meeting with a friend for a bike ride or brunch. In fact, she recently launched the Vineyard Icon Awards, a celebration of important changemakers, from cultural leaders to public servants and innovators, all of whom have deep ties to the Vineyard and an impact that reaches far beyond it.
Quintessential vineyard fashion styles were on full display at this inaugural event and will continue through the rest of the summer and into fall, as the island reaches peak tourism. When it comes to what to wear on Martha's Vineyard, Goldson encourages visitors to forget formal and embrace cozy instead.
'Vineyard style is all about ease. It's comfortable, light, and summery. Think whites, soft blues, pastels, and the occasional pop of color,' she says. 'What I love most is that you can wear a breezy dress during the day and change into a hoodie and jeans at night. It's chic without trying too hard.'
I've always admired Goldson's fabulous lifestyle, so I was excited to have the opportunity to pick her brain for her 14 go-to styles to wear on the Vineyard, from flowy dresses for an al fresco dinner to a comfy skort that will suit a bike ride to the beach.
One essential casual outfit that Goldson recommends for any coastal vacation is a reliable midi dress. This Quince smocked dress is made from organic cotton, so you know it will be soft and comfortable, plus it has a fun eyelet detail on the skirt. The relaxed fit and functional side pockets make this dress a versatile staple you'll wear over and over again.
Coastal getaways require a cozy layer, even in the middle of August. For chillier evenings, Goldson always packs an oversized denim jacket or hoodie. 'A jean jacket is a go-to staple for when the sun goes down and it gets chilly,' says Goldson, adding that she loves watching the sun set on the lagoon where she lives. This Madewell denim jacket is a collarless option with relaxed drop shoulders for a casual fit. Light enough to wear on any summer night, it pairs well with your favorite dress or flowy pants.
What's a coastal getaway without a trip to the shoreline? 'I love a full beach day with family and friends. Whether we're at State Beach, the Inkwell, or up island at Great Rock Bite, I always bring a cute beach bag and a cover-up that makes me feel pulled together,' Goldson says. The Versa Rubber Tote Bag is a perfect option for anyone who is looking for a fashionable, spacious bag. The waterproof and washable tote features a scalloped edge and comes in a number of vibrant hues, including colorful options perfect for the Vineyard, like tangerine and coral pink.
For any outdoor activity that requires good foot support, New Balance's DynaSoft sneakers will provide plenty of stability for long walks, bike rides, and everything in between. A durable rubber sole and plush cushioning create a sturdy foundation for all-day wear, and the no-sew upper makes this shoe easy to slip on and off.
A casual outfit for outdoor activity is also a must on Goldson's Martha's Vineyard packing list. 'One of my favorite things to do on the Vineyard is get up around 5 A.M., ride my bike to the Inkwell in Oak Bluffs for sunrise, then head toward Edgartown and return just in time to watch the Polar Bear swim,' she says. 'Since I'm rolling right out of bed, I need something that's quick, comfortable, and still cute if I bump into someone I know (as that is par for the course on MV!)' Old Navy's CloudComfy Cami Short Bodysuit is ideal for its super soft and stretchy material. It also features adjustable straps and a built-in bra so that you can throw it on with ease.
Coastal towns make it easy to get outside and get moving. Activewear should be a staple on any packing list, like this Athleta skort that comes with sewn-in gripping material to keep the undershorts from riding up. Plus, it has four pockets to store essentials so you can head out the door without a purse. 'The best part of the Vineyard is how a long walk or bike ride can lead to a full day of unexpected pit stops. I love workout clothes that work for a long bike ride, but feel polished enough to stop by a friend's house,' Goldson says.
Goldson always packs a cute cover-up for beach days. She recommends choosing one that can double as a dress if you want to grab lunch after the beach, like Blooming Jelly's Casual Cover-up. The lightweight V-neck option falls above the knee and features two pockets to store items like your wallet and keys. The loose, swinging style is ideal for days full of activity, too.
Vuori's Halo Modern Full Zip Hoodie provides all of the super soft Dream Knit fabric that the brand is known for, with a relaxed fit and length that allows you to layer your favorite shirt under it, perfect for the warm days but cooler evenings on Martha's Vineyard. The moisture-wicking material and four-way stretch are also clutch if you plan to wear it on a more active day to keep you dry even if you get sweaty.
A breezy maxi dress is a classic staple for any coastal retreat. J. Crew's Smocked Maxi Dress offers all the comfort of a classic summer dress with a cotton fabric that's ultra lightweight. 'Choose pieces that let you sit comfortably, move easily, and still feel stylish,' says Goldson. 'Some of my favorite Vineyard moments are dinners at family friends' homes. Whether it's ribs at the Murrays or the Fourth of July at the Crews, the vibe is always relaxed but still festive.' This smocked dress is a comfortable option for dressing up or down, so you can wear it to see where the day takes you. $298 at Fredasalvador.com
One of the best parts of an island getaway is that you never really need heels. Goldson suggests wearing flats that offer both comfort and flair, like Freda Salvador's Fisherman Sandals. The shoes are embedded with real flowers in each panel, and they have leather sole for increased durability. 'I never pack heels with me, even though I swear by them back in NYC. Think flats with woven textures, a splash of color, or a subtle platform,' she adds.
At this month's inaugural Vineyard Icon Awards, Goldson brought the best Vineyard looks to the event. 'The dress code was Vineyard chic—long dress, flowy, but definitely a statement piece,' says Goldson. 'As a fourth-generation Vineyarder, this is more than an event. It is my way of giving back to a place that shaped me. This island is part of my legacy, and this celebration is an extension of that.' Her final look for the event was inspired by soft floral and pastel prints like this Danica Strapless Dress from Bec + Bridge. Made from a delicate mesh material, the dress features chic touches like a cascading side ruffle and a statement keyhole cutout at the bust.
Pack something that can take you from day to night, like a cute cropped tank. This OnlyStory tank is made from a stretch round fabric that provides all-day comfort. A backless cut and side slits make it the perfect evening top to pair with your favorite skirt or pants. Goldson recommends pairing a tank with a casual, loose-fitting pair of pants like AGolde's Low Curve Fray jeans, made from supersoft, regenerative cotton.
'August is filled with events on the Vineyard,' says Goldson. There's always something to attend, from panels to parties. Having a small statement bag like this rhinestone clutch from BabeBeyond allows space for your personal items to be stored and doesn't take up too much room in your luggage. It features both a zipper and two circular handles, making it easy to tote around in style. $215 at Generationloveclothing.com
For a fun Sunday brunch or sunset happy hour with friends, the Mina SLace Shirt from Generation Love checks all the boxes for comfort and style. The popular classic button-down silhouette in sheer topaz lace truly makes a statement without trying too hard. You can dress it up or down and wear it open or closed. No matter how you style it, you're bound to get a compliment or two.
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