Your Guide To Dressing For The Hamptons

New York’s summertime playground, the Hamptons, are a destination for weekenders looking to chill out from the city’s daily grind and slip into relaxation mode. For those lucky enough to score a Hampton house, the summer is filled with some of the world’s most gorgeous beaches, old maritime charm, windmills galore, and fresh produce for those day-to-night barbecues. Fine dining, nightclubs, art and antiques offer more than beach vibes, making the Hamptons a culturally rich relaxation experience. As such, you’ll need to dress accordingly, catching the nuanced styles of each part of the island. To bring you a guide to dressing for the Hamptons, we partnered up with our friends at The Outnet, so let the island hopping begin.

White Heat

The official season of white kicks off after Memorial Day, giving you a chance to showcase white hot looks. The key to wearing white is to keep your look minimalist, but do don a splash of color with your accessories. Don’t be afraid to go head-to-toe in white; that look is totally chic. Do make sure your white is so fresh and so clean. This look is perfect for a visit to Sag Harbor’s charming Whaling Museum, or a visit to Easthampton’s LongHouse Reserve, an al fresco museum that’s off the beaten path.

Frontier Fashion

Iro dress, Stella McCartney jumpsuit, Mabu by Maria BK sandals, Iris and Ink espadrilles, Manebi espadrilles, Maje playsuit.

Going boho will work in Bridgehampton and Sag Harbor, not to mention Montauk, the end of the isle where you have to check out the working lighthouse. Dressing for the occasion, you can elevate the look beyond peasant tops and maxi dresses to conjure the subtly of prairie chic. What’s prairie chic, you ask? Think Laura Ingalls Wilder meets Carrie Bradshaw. This look is perfect for a trip to Gosman’s Dock in Montauk, a historic landmark with delicious bites.

Hampton Classic

Mary Katrantzou jumpsuit, Elizabeth and James mini dress, Oscar de la Renta espadrilles, Dolce & Gabbana bikini, Malone Souliers sandals, Emilio Pucci maxi dress.

For those who find wining and dining at posh restaurants, bars, and nightclubs the ultimate form of relaxation, there are plenty of options in the Hamptons. A day trip to the vineyards at the Wölffer Estate in Sagaponack. Your look should be polished but retain a summery edge that takes you from Main Beach to 75 Main. A chic sandal pulls the look together to get you a table at EMP Summer House and past the velvet ropes at AM Southampton.

Get Physical

For others, salt air inspires a sweat session on your Hamptons respite. Performance-enhancing workout gear that looks stylish is a must. From the tennis court to the yoga studio, to running barefoot along the beach, getting athletic in the Hamptons is a relaxing treat, whether you’re running to Crossfit in Southampton, the East End Tracy Anderson pop-up, or getting your Namaste on at Yoga Shanti in Sag Harbor.

Suit Chic

Nothing caps off a day at Montauk’s Surf Lodge or Bay Beach better than a bonfire. One-pieces are all the rage this season, making your transition from day time adventures to nighttime misadventures easy peasy. Paired with a mini skirt, shorts, or wide-legged jeans, your swimsuit works well after you’ve toweled off. Keeping it casual but classy, this look is ideal for a nighttime walk on Sag Harbor’s Long Wharf, where you can get frozen cocktails and the best waffle cone in town.

Sheer Pleasure

Sensi Studio mini dress, Emilio Pucci cover up, Dolce & Gabbana cover up, Melissa Odabash maxi dress, Celia Dragouni maxi dress.

Want to cover-up and stay cool at the same time? Sheer fabrics do the trick while making sure you stand out in a crowd. Whether chilling poolside at the Shelter Island House or running to town for some last minute provisions, a chic and sheer cover-up is a must for all your Hamptons adventures. Feeling too bare? A caftan-style cover-up has you, well, covered.

Time to Unwind

When the sun sets, and the grill is fired up, all you have to do is slip into something a little more comfortable and you’re ready to enjoy all the fruits of the island — be sure to visit the Amagansett Farmer’s Market, or the Country Garden on Millstone Road. Pair a bikini with a cover-up or jumpsuit and slide into cocktail hour without missing a beat. No matter where you are on the island, you’re in relaxation mode now.

About the author

Jill Di Donato

Fashion Editor

Jill is a New York native who holds a BA in Literature from Barnard College, and an MFA in writing from Columbia University. She is the author of the novel Beautiful Garbage (She Writes Press, 2013) about the downtown Manhattan art and fashion scene in the 1980s. A former staff writer for The Huffington Post and Bustle, Jill comes to Culture Trip after working with Refinery 29, Vice, Salon, Paste Style, Los Angeles Times, Nylon, Shopify, Autre, and producing content for emerging fashion labels. She teaches classes about fashion and culture at Barnard College and The Fashion Institute of Technology. Her prized possessions are her Gucci fanny pack, vintage rocker t-shirts, and her grandmother's collection of costume jewelry. She's always on the lookout for a gem-encrusted turban.