How to Dress for the Hamptons*

* Without looking like you're dressing for the Hamptons.
Photo: Courtesy of the Author

Once you've nailed the look, take care to be photographed on the beach in wispy, nostalgia-inducing gray light: The author with son Heathcliff and wife Lucy.

My wife and I, along with our two sons, live in a small West Village apartment during the week. It’s basically a dormitory from which we head daily to school and office—and restaurants, store receptions, and the odd benefit gala. We have a kitchen table, big TVs and internet access. It’s good.

And yet most every Friday, year-round—and sometimes on Thursdays when we can concoct a good excuse—we drive at great speed through the Midtown Tunnel and 100 miles east of the city, to Bridgehampton. There we keep an old cottage, built in 1760 and enhanced by odd additions every 50 or 100 years thereafter. We prefer that our weekends last at least until 6 a.m. on Monday.

While there we take care to dress appropriately.

In Bridgehampton, this means a devil-may-care elegance. The place is about authenticity, and that precludes wearing one label head to toe. A little Ralph Lauren is always a good thing—my old girlfriend, Amanda Brooks, got me hooked on his cable-knit cashmere sweaters—but a real prepster is always, instinctively, as much punk as label whore.

As for me, I tend to wear more colors, and brighter colors, at the beach than in the city. Not too lurid though: dark reds and greens, and a bit of powder blue if I’m in a good mood. I also make sure to appear artfully disheveled, because there’s nothing worse—nothing at all—than looking too put together at the weekend. Your Nantucket reds should be faded. Your docksiders should be salt-caked. Your polo shirt should stay untucked, and should not carry a logo on its breast. (As an aside—and I’m aware this is an upper–middle-class English affectation—please don’t throw out a wooly sweater just because it has a hole on the elbow. Ask someone to darn it for you, or put a patch on, or best of all, just leave it be. It will be cozier and cooler, in every sense of the word.)

Photo: Patrick McMullan Agency

6 a.m. on Monday? Still five solid hours away!

Speaking of polo shirts, my friend Sean Mahoney has his tailored by our go-to guy: Fabrizio Volterra at David Chu Bespoke. He might be taking it a bit far, but he always looks good at the weekend. Sean works very hard to dress like he doesn’t care.

Make sure you check Gilt MAN mainstays Steven Alan, Rag & Bone, and John Varvatos—you could buy all your clothes from those three labels and you’ll be dandy through Labor Day. Think canvas jackets and lots and lots of lightweight cotton. I like to layer on the weekend, with paper-thin T-shirts and lighter-weight chinos that might sensibly be a little baggier this year. I’ve been sporting the fashion editor/hipster roll of the pants; if you’re going to roll up your shirt sleeves, might as well show some leg too. Shorts are fine, in any color, but they must be made of cotton and be neither too short nor too long. No statement shorts please. And I’m bored of board shorts.

You can go the jeans-and-sneakers route, but they should, again, be pretty well worn in. I love my Converse by John Varvatos—picked up cheaply, in large quantities, from Gilt—but please don’t wear running shoes to the supermarket. Ever. I hate that pristine, lycra–coordinated sportswear look, even on the hot moms grabbing coffee at Golden Pear on Sunday morning.

Up top, a linen or cotton jacket is good. A blazer is also fine, but only if it fits well. Think new Brooks Brothers, not old Brooks Brothers. And wear it casually—you’re not going to play golf or going to the country club. At least I hope you’re not. You’re going to walk on the beach, and eat barbecued meat, or hamburgers at Bay Burger, and then drink Martinis at the bar of World Pie.

I suppose I’m now old and fuddy duddy enough to prefer my shirt to have a collar, at least if I’m sitting down to dinner. I like wearing a proper dress shirt. Creased is nice with the sleeves rolled up, but I hate that half-rolled look which displays only the wrist bones.  If you’re going to roll up your sleeves, just bloody well do it.

And to pontificate, finally, on a subject of great import and abiding interest to Gilt Manual editors—if not their readership—I really don’t mind in the slightest whether you wear socks or not.

Shop our Summer in the Hamptons sale on Gilt >

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