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Whether you are celebrating virtually, at home, or with a few loved ones, this dress is good for now in our more casual climate, and the future when we can all gather! (Runs tts and goes up to a 3x, if in-between, size down. I am in XXL). 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. Did you know grape vines get fall foliage like trees?!
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.
Scalloped Tiered Dress
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.
It’s so dang cool to wander the vineyard rows during the fall and view the colors. On top of a top-notch deodorant, I always reach for sunglasses, sun hats, straw hats, flowy dresses, and linen jumpsuits. I like to channel Greek island vibes sometimes — big dresses that billow in the wind and help cool me off while still looking effortless. This will be the time of year that I wear shoes I’m ready to get dirty, since it may be muddy in the vineyards.
Stretch Cotton Twill Plaid Shirt
You won't be able to say inside the lines, with these new colorful arrivals from Vineyard Vines! Not all wineries seat you for tastings, so you have to expect you’ll be standing for most of the day. Wine plus high heels and standing for hours already is a recipe for painful feet, but add in uneven terrain and you’re be wishing you wore something else.
And one thing I really love about women’s Martha’s Vineyard style is how timeless Martha’s Vineyard outfits are. This past fall I wore my favorite white maxi dress while wine tasting and I spilled a little red on it. I was so sad, but thankfully the winery had Wine Away. This stuff is magic and makes wine stains disappear fast!
When In Doubt – Go With A Simple Outfit
You’ll also receive better service if you dress up vs down. 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.
Again, these are all the exact items I own and pack for my annual trips to Martha’s Vineyard . 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. This year, I added this specific ruffled pullover from Tuckernuck and a striped half-zip sweater to my own personal closet.
I hope this helps you get ideas on what to wear to a winery! I’m not going to lie — I love looking at what other bloggers are wearing to get updated wine tasting outfit ideas. I don’t think I’ve ever had a hot winter wine tasting experience.
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.
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.
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.
Stay all day lipstick is KEY when wine tasting and eating cheese for 6 hours straight. I found this lipstick last year when looking for one that stays put under my facemask and I know it’s going to be my favorite lippy when I go wine tasting again this summer. 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. 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. Lastly, to get some head-to-toe women’s Martha’s Vineyard style inspiration you can buy.
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