Since President Obama and his family are here on Martha’s Vineyard, (not that we’re hanging out or anything), I’ve been giving some thought as to what people should wear to events here, specifically weddings.

“What should we wear” is the second question I get from off-islanders regarding weddings, the first being: “how many beds do you have for our extended family?” (My official answer, “Our septic system can’t handle any guests, and you don’t want to find out why.”)

To tell you what to wear to a Vineyard wedding, I need to know two things: who is it, and where is it?

If the wedding is “up island,” (in rural, expensive Aquinnah or Chilmark), then the next question is: Hippy or Hollywood?

If it’s Hollywood, you can count on gorgeous views:

Tons of charm, great food, lots of well-organized assistants and heavy security. I recommend that L.A. “wealthy boho” look you can find at Calypso St. Barth.

It costs a fortune, but you know you can make something like that. Please note that the wedding will probably take place under a tent in a field something like this:

So wear flat shoes that won’t sink in the grass and will protect you from ticks and manure. And make sure that your dress can be pulled up easily in a porta-potty, because there’s going to be one.

If it’s a hippy wedding, odds are good you’ll be peeing in a field, so dress accordingly. If they ask you to bring food, do it. As a matter of fact, I’d eat first and bring a flask of Sancerre. Seriously, you can wear anything, even this:

(Doesn’t that rope thingy look like something midcentury sculptor Isamu Noguchi would have designed for a Martha Graham dance about yachting? It was about as expensive as a Noguchi, too.)

There’s a lot of poison ivy up island, so again, your footwear should be flat, disposable, or hose-able. Lily Pulitzer Crocs would be good. During one particularly bad October deluge, the bride resorted to wearing her garden clogs down the aisle.

And for any wedding in a tent or field, you need good bug spray to ward off the ticks that carry Lyme disease, and a WARM wrap or jacket for after the sun goes down.

Now let’s head “down island” for a wedding either in Edgartown (permanent host of the Preppy Olympics) or any place with the word “Club” in it.

Let’s look at Edgartown. Beautifully manicured Captain’s houses:

Gorgeous New England seaside gardens:

And ample places to buy the preppy uniform of whale pants, polo shirts, breton shirts etc…

For this type of wedding “weekend,” bite the bullet and fit in. If you just landed from planet “not preppy,” you could go to this store and be all set:

A pretty teal dress for an afternoon wedding, white jeans and Breton shirt for whatever lunch/brunch comes your way, and a featherweight lavender cardigan for anything outdoors.

As for the khaki shorts on the left, at my Vineyard wedding 20+ years ago (at an inn with an outdoor wedding venue but indoor plumbing, thank you very much) a plus-one guy from Edgartown showed up in an oxford cloth shirt, docksiders, the ubiquitous preppy navy blazer and khaki linen shorts. Shorts! At a wedding! Mercifully for him, I can’t recall his name.

On that same afternoon, the power went off all over the island, including at the hairdresser, sparing me from looking at wedding pictures with a giant 80s bouffant hairdo. It was fate! (Note: between the salt air and the wind, everyone’s hair looks terrible on the Vineyard, so don’t worry about making an effort.)

As for weddings in the other regions and cultures of the island, where the wedding could be in the tin-roofed Tabernacle:

Or in the sand:

Best to call the mother of the bride and ask. She’s probably dying to vent.

One last question about Edgartown. Is the wedding at the Whaling Church?

It’s gorgeous, historic, either too hot or too cold, and has the most uncomfortable seats on the planet.

For your sake, I hope the wedding looks like this:

Okay, that wasn’t actually a wedding. It was the Official Blues Brothers Revue, doing a fundraiser for the Vineyard Playhouse. The gorgeous trompe l’oeil painting on the back wall was done by talented Vineyard muralist Margot Datz.

While I was at the concert, sitting with boomer-age friends who, in the 70s, toured as recording artists, lived with famous musicians, and spent quality time alternately crashing in Teepees or on lumpy NYC futons, ALL we could talk about was how happy we were that the Whaling Church had new, thicker cushions for our aging bums! And even with better cushions, my sitz bones were killing me! So bring a wrap, even if it’s hot, because you’re going to need to sit on it.

And enjoy the Vineyard. Really, there’s a reason why presidents have been coming here for more than a century.