The Hamptons have a certain patina to non-native New Yorkers. Before my first trip, I envisioned it as a big hedonistic party, snob central for Page Six fixtures, and prohibitively expensive for anyone without a Maybach at their disposal.
My first weekend in the Hamptons was in 2009, the summer I moved to New York from Florida. And I packed ALL the wrong outfits, including a skintight fuchsia Nicole Miller dress and matching magenta Missoni stiletto sandals. (I blame Sex and the City and The Great Gatsby for these miscalculations.) Dressing too formally is a rookie move — too gauche, too obvious and too desperate for approval.
Most of the Hamptons have more in common with sleepy Florida beach towns than glitzy St. Tropez. When my friend Daniele invited my husband and I to join her family in Sag Harbor last weekend, I made sure to keep my weekend bag light and tight, with plenty of appropriate outfit options.
Layering is crucial. The Hamptons can be blazing in the sun and downright chilly on the windy beach. I relied on interchangeable, elegant basics so I could mix and match on the fly.
Here are the power pieces I milked for maximum mileage this weekend:
- Gray Alexander Wang sweater: Extra-thin wool and comfortable as a tee. An unusual cut and construction blends well with casual or dressier outfits. (Photos 1 and 3)
- White Juicy Couture linen pants: Lower maintenance than white jeans for trips to town. Warmer alternative to a short beach cover-up. (Photo 2)
- White flea market lace top: More special than a plain tank top, but just as easy. (Photo 2)
- Zara denim jacket: The ultimate layering piece. Pick a snug version, and it doubles as a chambray shirt in a pinch. (Photo 2)
- Pale Pink Marc Jacobs dress: The flounced skirt borders on being too dressy for a beach weekend, but I cut through the treacle by layering a gray sweater on top. (Photo 3)
And you only need one pair of jeans, shoes and swimsuit:
- High-Waisted Madewell denim: Plenty of stretch to counter back-to-back BBQs. (Photo 1)
- Beaded Stuart Weitzman sandals: More elegant than a flip flop, but still made from rubber, so no worries getting them wet. (Photos 1, 2, 3, 4)
- J.Crew bathing suit: I just hang it outdoors to dry overnight. (Photo 2)
I’ll be posting more packing lists and tips under the new What to Pack category. But for now, I’ve included a Hamptons cheat sheet that will help neophytes determine each town’s personality — and subsequent sartorial tweaks. (Guide is courtesy of my friend Daniele, a lifelong Hamptons weekender.)
- Westhampton: Doesn’t count as the Hamptons. (Too close to the city.)
- Hampton Bays: Home to the seasonal workers who cater to Hamptonites. Many NYC professionals on the younger end of the spectrum get their house shares here.
- Southhampton: Old money. Country Clubs. Tennis whites. Saltwater taffy. The quintessential New England town.
- Bridgehampton: Horse country. The biggest attractions are the restaurants: Bobby Van’s and Pierre’s. (But if you can afford a $27 sandwich, you probably have a personal chef at home.) Least crowded of the beaches.
- Sag Harbor: The artsiest town in the Hamptons, with minimal Manhattan influence. You won’t find a Tahari or Tiffany on the shopping strip — but I did spot a consignment shop selling a $16,000 secondhand Birkin.
- East Hampton: New money. Also home to Tory Burch, Lululemon, Starbucks and the Hamptons’ most crowded beach. The average wait time for a dinner reservation is 2 hours and 15% of your dignity.
- Amagansett: Increasingly popular destination, but still pleasantly sleepy. A respite between the East Hampton scene and the Montauk chaos.
- Montauk: Party central. What was once a quaint fishing town has now been overrun with night clubs and bachelorette parties.