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Epic Women’s Martha’s Vineyard Style Guide with Outfit Ideas

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This post shares exactly what you should pack for Martha’s Vineyard from someone who visits every year!

Women’s Martha’s Vineyard style is unique with a distinct look: preppy, nautical and Americana, but with more casual sensibilities than upper crust neighboring island, Nantucket.

It’s the type of place for which you want to pack certain specific Martha’s Vineyard attire and Martha’s Vineyard outfits when you are visiting: like hats for windy breezes and pullovers for chilly mornings, not to mention boat shoes for your sailing adventures!

martha's vineyard style collage
striped pullover / straw hat (POPULAR) / gingham sweatshirt / wicker purse / American flag sweater / baseball hat / striped dress/ boat shoes / striped boatneck shirt / tote bag

Over years of visiting Martha’s Vineyard each Summer, it has informed my own style as a whole. And one thing I really love about women’s Martha’s Vineyard style is how timeless Martha’s Vineyard outfits are.

This women’s Martha’s Vineyard style guide discusses Martha’s Vineyard outfit ideas; brands located in the Vineyard and/or whose style works well there; specific Martha’s Vineyard attire recommendations by category and print; and head-to-toe outfit ideas you can buy.

I share exactly the products I own, love, and pack myself when I go to Martha’s Vineyard.

How Should I Dress in Martha’s Vineyard?

Martha’s Vineyard outfits maintain a classic and preppy look, with hints of nautical and Americana inspiration. You should pack: sweaters and sweatshirts, as well as hats and long pants for cooler, windy temperatures (even in Summer).

Some Martha’s Vineyard outfit ideas are to bring a few classy pastel dresses for days or nights on the town. Prints such as blue and white stripes, gingham and madras work well.

Consider brands like Vineyard Vines and Lilly Pulitzer, which are most popular there.

Women’s Martha’s Vineyard Style Brands

The following brands are either located in Martha’s Vineyard or have items that bear the distinctive Martha’s Vineyard attire. I regularly shop them all and love them!:

Women’s Martha’s Vineyard Outfit Ideas by Categories

Below are specific women’s Martha’s Vineyard outfit ideas by category of the most popular women’s Martha’s Vineyard style, followed by pictures of my favorite products I own and love (or similar styles) for you to shop:

Blue and White Stripes

Blue and white stripes are so nautical and, therefore, are crucial to your Martha’s Vineyard outfit ideas. It’s a classic print that looks good on everyone, whether it’s navy, seersucker or some other shade of blue.

I have a midi striped t-shirt dress like this Vineyard Vines striped dress and one like this Draper James striped dress that I get so much wear out of.


Besides blue stripes, gingham is arguably the most preppy print that will always fit in on the Vineyard and will never go out of style.

I always pack this Draper James sweatshirt and a purse similar to this Draper James gingham purse.

Related post: Guide to gingham

Hats (Straw & Baseball)

It’s breezy, if not windy, year-round in Martha’s Vineyard, so hats are not just a fun preppy accessory but a must-have.

I have this specific packable wide bow sun hat from Tuckernuck and love it! It’s monogrammable and sells out every single year (so if it’s available and you like it, buy it!). The quality is fantastic for the price. And It’s also really popular with my readers!

I always pack a Vineyard Vines women’s baseball hat as well (these particular hats fit really well and look good). Another place to consistently find great women’s hats is Gap.

Tote Bags

Tote bags are functional fashion accessories to Martha’s Vineyard outfits. Load up a classic canvas one from Vineyard Vines or L.L. Bean to use as a beach bag or for a stop at the farmer’s market.

I added this specific Madewell woven leather tote to my collection this year, and I think it’s the perfect look at a reasonable price point.

What to tote: The Best Books Set in Martha’s Vineyard

Straw & Wicker Purses

Bicycle baskets are abundant in Martha’s Vineyard, and so straw and wicker purses perfectly echo this Island staple. Like most women’s Martha’s Vineyard style, they never go out of style.

For so many years, I’ve had one like this Wicker Wings bag from Tuckernuck that I love and always gets compliments.

Sweatshirts and Pullovers

It’s always chilly in Martha’s Vineyard, so sweatshirts and pullovers are preppy, casual necessary Martha’s Vineyard attire. A quintessential Summer morning stroll is best equipped with shorts and a pullover!

I’m a huge fan of pullovers. My drawers are literally filled with them, and they are perfect for Martha’s Vineyard outfits as well.

This Lilly Pulitzer Skipper popover is a staple in my closet, as well as the classic Vineyard Vines Shep shirt.

This year, I added this specific ruffled pullover from Tuckernuck and a striped half-zip sweater to my own personal closet.

Boat Shoes

Boats are plentiful in Martha’s Vineyard, and chances are you will be on one or more during your stay, so classic Sperry boat shoes are a must!

I wear the Sperry Angelfish, which is more feminine than a classic boat shoe and very plush inside. They are super sturdy, so sometimes I wear them in times I would wear a casual sneaker.

They run true to size for me, but their classic boat shoes run 1/2 a size large on me. I’ve had them for years, and both the style and shoe itself have stood the test of time.

Patriotic Style

Martha’s Vineyard attire is often represented with patriotism. American flags are everywhere you look!

The best way to sport this style is with this classic American flag sweater from Tuckernuck.

Boatneck Shirts

Boatneck shirts are so classic and so flattering. And since they often come in stripes, they give off Americana vibes that are so plentiful in Martha’s Vineyard outfit ideas. I have several, and I consider this to be a staple closet piece.

Currently, my favorite style is this Vineyard Vines boatneck tee.

Related post: J.Crew Capsule Wardrobe

Golf / Polo Shirts

Martha’s Vineyard attire is preppy, and there’s arguably nothing more preppy than a golf shirt. It’s great on its own or as a layering piece, for just about anything … including golfing of course! There are several popular courses on the Vineyard for golf lovers.

My favorite golf shirts are from Vineyard Vines and bear a little blue whale emblem on the chest.

Beach Coverups

If you are visiting Martha’s Vineyard in the Summer, you will likely be spending some time at the beach. Since you may be biking from town to town or hopping around the island, it’s nice to have a good coverup to take from the beach to town. And since it’s often chilly on the Vineyard, you may even end up wearing your coverup on the beach (I often do!)

My favorites are from Lilly Pulitzer because the pretty prints make them look like dresses! (I was wearing one when I got engaged in Martha’s Vineyard!)

I think you will also love this Lilly Pulitzer Martha’s Vineyard beach towel. I have the matching pouch.

Waterproof sandals like these Freedom Moses sandals are also a popular choice.

Martha’s Vineyard Outfit Ideas

Lastly, to get some head-to-toe women’s Martha’s Vineyard style inspiration you can buy. Again, these are all the exact items I own and pack for my annual trips to Martha’s Vineyard (or very similar styles).

Scroll through and click below to shop some swoon-worthy preppy fashion:

How to Dress in Martha’s Vineyard in the Off-Season (Fall and Winter)

If you’re visiting Martha’s Vineyard in the off-season, these classic style posts may help you:

That’s everything you need to know about women’s Martha’s Vineyard style!

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Judith smith

Sunday 4th of July 2021

Nice article about MV style. The Vineyard is an Island consisting of several towns. Accordingly, you are “on” the Vineyard having lunch “in” Edgartown or Oak Bluffs.


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