| Going for a few days with family. I assume not everyone is preppy as I went to Martha’s Vineyard and felt very overdressed with “preppy” attire and everyone was very laid back and relaxed. Tees and shorts type vibe. |
| Omg please stay away. |
+1 Well I guess for one they don’t dress like cosplaying influencers |
| OP stop being weird and trying too hard. Just wear regular clothes. I'd definitely bring LAYERS. |
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OP, I’ll give you the benefit of the doubt. You probably just don’t want to be out of place, which I totally get.
If I were you, I would subscribe to the Instagram hashtag #ACK. That’ll show you photos of people who are there and tagged that hashtag. I’ve never been, but my view on the attire is less hard-core preppy (martini glasses on actual Nantucket Reds), but more just a general, relaxed New England prep. |
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I was recently in Nantucket. Dress normally! There is no "uniform" as displayed on social media. There are cobblestone streets everywhere so wear practical shoes such as sneakers or Birkenstocks. Shorts and t shirts or sundresses.
Most people were walking around in sneakers or athleisure, in addition to casual sun dresses. |
Eww |
| It's more formal than MV. Preppy works but no need to overdo it. Chic is always welcome |
| 🤦♂️ |
Do you realize this means nothing to people? You need to give specific examples. |
| It is no different from DC. Just wear what you would normally wear in cold spring weather. |
| The Instagrammers or the people who have been there for generations? The latter? Eh, what the former would consider slobs. It's kind of a "if you know, you know" thing. "Fitting in" for a one week vacation isn't a thing. Wear whatever you want. |
| If you are going to be going out to dinner, dress sharply. Think Morley or Sassanova. During the day, dress casually but pulled together. Think Frank & Eileen. |
| Lots of logos and bright, loud colors. (Kidding) |