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Leandra Medine, writer and founder of Man Repeller, is a regular at New York’s Southampton. Here, she shares her insider tips on what to see and wear while you’re there.

Welcome to the South Fork of Long Island where the clams flow like Bottega Veneta shoes at fashion week and the preferred method of body covering implicates as many layers of white linen as one can find.

The Hamptons, Long Island
The Hamptons, Long Island

The Hamptons get a fairly bad rap given the associated implications of snootiness and gargantuan home-ness – the Fitzgeraldian West Egg-ness that brought Gatsby to his knees – but there’s another side to it. I should know, I’ve spent more than 20 summers on the East End as a dependent resident of the Shinnecock area of Southampton, where the homes are more like cabins in the woods and the pursuit of solitude – so sacred in Manhattan – is not really a pursuit, it’s a given. The thing you just get when you’re there. No shoes? No problem. Walk barefoot on the grass that is occupied by the orchestra of crickets that begin to play at sundown. Open a bottle of wine and make it natural – Jobs Lane Wine & Liquor now carries varietals. Throw a burger on the BBQ or some lettuce into a bowl (and use Bordallo Pinheiro flatware – this way your Instagram tablescape can speak for itself; no caption necessary).

Of course, this is supposing you’re a guest of someone’s home. If you’re not, that’s fine, too. Might I suggest Southampton Inn, just off Main Street? Or the American Hotel in Sag Harbor 20 minutes further east? There’s also Topping Rose in Bridgehampton, or the Inn at Windmill Lane in Amagansett. Should you venture so far as to surftown USA – the artist formerly known as Montauk – there’s only Crow’s Nest. I mean, there are plenty more places to stay, but there’s only Crow’s Nest. You take a room, leave your shoes at the door, and come out to watch the sunset on the water. Once it’s gone, food hour begins! Get the mezze platter, then find your shoes (and a car) to drive to John’s Drive-In for ice cream. Authentic and creamy and sugary and milky, there is no ice cream like it.

Inn at Windmill Lane, Amagansett

Save for, that is, Big Olaf’s in Sag Harbor. If you’re a bit further west and out for pizza at Sal’s, you might want to drop by after your meal. What you’re wearing doesn’t matter, but it also doesn’t change. If I were you, I’d wear a pyjama set that could also be a cover-up – what you put on is also what you take off, and I’ll make a case any day of the week for Asceno’s silk suits, beach or dinner side.

I’m throwing in a bathing suit for good measure, too, now we’re two outfits down and in the scheme of this weekend, still have a full day to go! You’ll need a place to keep your stuff, so consider Dragon Diffusion.

Amagansett’s best bet for a meal? You have to try Carissa’s. Take it to go and eat it on the beach. Wear a sequined bikini because it’s basically an outfit, add a pleated white skirt and call yourself ready to head west. To The Egg, that is – Southampton village at dusk. You don’t have to change, you’re wearing the right clothes, but keep a cardigan nearby. Add flip-flops from The Row, or stay grounded in your Birkenstock X Il Dolce Far Niente. That choice is yours, but take it when I recommend the back garden at La Parmigiana. It’s an institution, more casual than you’d believe, and a good bowl of pasta, all but drenched in olive oil. When you’re done with that, consider what plans you have on tap for the next day.

Medine with her mother in Southampton

Nothing? Oh good! Hit up the farms – all of them. Roundswamp, Amber Waves and Hank’s, in particular. The produce is so fresh you can practically smell the rasp in berries. Take them to the beach. And your tote is big enough, so here’s a contingency plan: a leopard-print one-piece, a counter-print sarong, and one more button-down, purely for good measure. I’m adding a hat, too, and now I believe it’s official – you’re practically a local.



The Style Report
The Style Report