4 Outfits for Hopping Around the East End

4 Outfits for Hopping Around the East End

As a tradition-loving location, the East Coast never strays far from its annual wardrobe staples. Every summer in the Hamptons, there’s lots of love for stripes and pretty much anything with a nautical theme. Denim makes an appearance on occasion, though rompers, trousers, and skirts are preferred. However, across Long Island’s South Fork, each village has a touch of its own style, which is especially true in Montauk as it often goes rouge by echoing surfer vibes from the West.

That said, here’s a brief breakdown of my favorite villages to visit when vacationing out East of the city, along with a look at what to wear while rubbing elbows with Hamptonites.

Sag Harbor

It’s all about playful, daytime activities here. You can brunch on Main Street, grab lunch by the Harbor, go boating, stop by a street side farmer’s markets and then go back to your house to grill out and lounge the night away. When visiting this coastal area, an easy, breezy day-to-night look is all you’ll need.

Some of my favorite spots to visit are Le Bilboquet (a seaside French bistro), Baron’s Cove (a hotel, also a good spot to take in the harbor view and a burger), and Page at 63 Main (the restaurant features organic veggies, plus a market in the back).

Outfit: Cherry print romper, Draper James // Espadrille sandals, Matt Bernson // Sunglasses, Quay // Hair accessory, Club Monaco

Southampton / Water Mill / Bridgehampton

Eat. Shop. Drink. (Bottle Service). Excluding the club scene (AM Southampton), a laid-back chic vibe works well for poolside hangouts and late afternoon lunches that are followed, of course, by plentiful shopping.

Some of my favorite spots to visit are Copious Row (a chic boutique in Southampton), the Eberjey and Sugarfina pop-ups in Southampton, Calissa (Greek food, which I could eat on repeat for life), Topping Rose House (a boutique hotel in Bridgehampton with a Jean-Georges restaurant), and Wolffer Estate Vineyard (in Sagaponack, but definitely worth the drive).

Outfit: Off-the-shoulder top, Bailey 44 // Cropped trousers, Mango // Sunglasses, Celine // Mule slides, Jeffrey Campbell

East Hampton /Amagansett

In East Hampton, you can find more great boutiques and dining. However, the further east you go, the more chill the vibes become. So in Amagansett, where a lot of weekend warriors are getting share houses, it’s more about dropping in for an all-day BBQ at a friend’s cottage (the word used for a 4-8 bedroom house on a minimum of one acre of land. lol). Still, when the sun sets and it’s time to leave the pool behind, you head to the bars. That said, you’ll want a look that can easily transition to live music dancing and beer clinking the night away.

Some of my favorite spots to visit are the Reformation Beach House (eco-friendly shopping) in East Hampton, Wölffer Kitchen (one of two spin-off restaurants from the vineyard), Harbor East (lobster roll, anyone?), and Stephen Talkhouse (the place for live music and beers). BTW – If you feel like ditching the parties and going out for fine dining instead, the EMP (Eleven Madison Park) Summer House pop-up is in East Hampton but good luck getting a reservation. This upper crust eatery has been booked up since before it opened.

Outfit: Cropped tee, Topshop // Skirt, Milly // Sunglasses, Quay // Mule slides, Jeffrey Campbell // Handband, Club Monaco


Beach. Bar. Chill. Enough said. Denim shorts and your favorite tee with ripped surfer feels are all that you’ll need here.

Some of my favorite spots to visit are Gurney’s (a hotel with beach cabanas and umbrella cocktails), Navy Beach (fish tacos and beachside tables stacked with rose’), Ruschmeyer’s (beers, bros, and lawn games), and The Surf Lodge (where cool kids go to listen to music and act like they don’t care about being cool).

Outfit: Denim shorts, Frame // Shoulder cut-out top, Bailey 44 // Sunglasses, Celine // Baseball cap, ’47 // Sandals, Givenchy

Location: The Hamptons

Photos: www.shkphoto.com






1 Comment

  1. July 12, 2017 / 10:01 am

    I’ve never been to the Hamptons but feel like I have been seriously missing out thanks to all of your recommendations! As usual I am loving ALL of you outfits.