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.
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.
Ski Blanket Harbor Fleece Shep 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.
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.
Shirt Fabric
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.
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.
Wear White With Caution
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.
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.
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.
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.
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?!
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.
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