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When autocomplete results are available use up and down arrows to review and enter to select. Touch device users, explore by touch or with swipe gestures. Helen and I have two different body types but we love to twin in a good, cheerful dress.
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. Anything that has layers and tons of warmth in case your wine tour takes you on a stroll through a cold wine cave or something. Always pack an umbrella, too, as there’s a good chance you’ll get winter rain! Keep in mind the vines will be dead and brown, so you probably won’t be taking too many wonder babe photos strolling the vineyards this time of year. Honestly, wine tasting is literally just fancy day drinking.
Harbor Fleece Shep Shirt
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. I always pack a Vineyard Vines women’s baseball hat as well . Another place to consistently find great women’s hats is Gap.
So, if you do insist on wearing white summer fashion outfits or wear jeans that are light-colored, bring a bottle of Wine Away with you. I always wear flats like loafers or slides, or baby chunky heels that are super comfy (like this pair!). For winter winery visits, I may even wear boots without heels. If you’re looking for wine tour outfits, it’s especially important to wear sturdy shoes as they’ll probably be taking you all over the vineyards, fields and caves. The perfect wine tasting shoes are ones you can stand all day in. Before we dive into this winery outfit ideas and guide, let’s talk dress code.
Vineyard vines outfits
It doesn’t matter where I am wine tasting or what season, there are some cardinal rules I follow when styling wine tasting attire to make sure I’m comfy . The best way to sport this style is with this classic American flag sweater from Tuckernuck. My drawers are literally filled with them, and they are perfect for Martha’s Vineyard outfits as well.
But mostly I just get really inspired by the romance of winery gardens and dress to match. Not all wineries stock this, so you should bring your own on wine tasting trips. I once spilled red wine on my favorite white dress and with a few sprays, the stain was totally gone.
Vineyard Vines
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. The forecast for my tasting is a heavy thunderstorm so the many open toe shoes don’t seem practical and August is still too summery for booties. Can you please expand with pictures on your “shoes I’m ready to get dirty” line above? I’m struggling with how to dress up shoes I’m ready to get dirty without secretly hoping nobody looks at my feet, lol.
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.
Blue and White Stripes
Vineyard Vines Men's Race Stripe Shep Shirt Subtle stripes add just a touch of style to the New Women's Vineyard Vines Striped Shoulder Shep Shirt.
You’ll be holding a wine glass and will need your hands free to open doors or take photos with your phone. Skip your Cult Gia bag and trust me when I say you’ll be grateful for a small hassle-free purse like this crossbody bag. Make sure it has an easy open top for you to reach in and out of, as again, you don’t have two hands to open a zipper or complicated button when you are holding a wine glass.
Vineyard Vines Blackwatch Velvet V-Neck Dress was perfect for A virtual gift wrapping party that would be so fun to do with friends. It’s classic and is a great dress for both now and later. With a gift wrapping party, everyone gets dressed up, you grab a few gifts you want to wrap, and at the end you show off your holiday creation. It’s a different take on a gift exchange that is more of an activity, with less to mail and coordinate in these times! Our Vineyard Vines’ Dresses are perfect for this holiday season because it is beyond comfortable. The velvet really elevates things, but it feels like a cozy and easy dress you could also curl up at home in.
I always pack this Draper James sweatshirt and a purse similar to this Draper James gingham purse. I share exactly the products I own, love, and pack myself when I go to Martha’s Vineyard. Wine tasting is so strongly rooted in your nose — sniffing the wine glass and tasting flavors. Strong perfume is going to mess with your taste buds, so just wear some good deodorant and skip the perfume. I think you will also love this Lilly Pulitzer Martha’s Vineyard beach towel. 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.
You’ll be tired and a wee bit drunk after a long day of sipping wines. Skip the button-up romper that is hard to take on and off, or the wrap dress that likes to blow around and instead just wear something simple and/or hassle-free. I gotta put that in caps because yes, I am internet shouting at you. I see women all the time-tripping around vineyards in high heels on their winery tours and it’s just not the shoe to wear.
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