I've never been to the Hamptons, but celebrity outfits have taught me how to dress like a Montauk local.
Hollywood's finest have been vacationing in the seaside towns of Long Island, New York, for over a century. They desert gated communities in Calabasas or Beverly Hills for the coastal sanctuary's old money charm, five-star seafood restaurants, and Michael Rubin's iconic "White Party."
Fashion girls don't just shift their schedules to be extra easy-breezy, but their personal styles, too. Color palettes have always taken a nautical turn toward creamy linen, sky blue denim, and all the sand-tinted raffia totes their luggage can carry. So, for the last few summers, I followed suit (except at an Airbnb in northern Wisconsin).
Hamptons sweetheart Martha Stewart has been my vacation blueprint for years. Oversize sun hats, linen button-downs, and patterned easy pants became her essentials in the mid-'90s. She stayed loyal to the hero items long after selling her 19th century cottage in East Hampton five years ago.
Two decades later, the Hamptons' street style scene is still just as strong. Each summer, a fresh pack of fashion FOMO sails onto my Instagram feed. This year, I'm heading into my mini Hamptons holiday with vacation outfits inspired by Stewart, Angelina Jolie, Jennifer Lopez, and more. Ahead, find my 8 favorite summer vacation outfits to recreate for Montauk or Southampton energy, no matter where you're traveling.
Martha Stewart's Hamptons Outfit in 1995
Martha Stewart is a living, breathing tutorial on how to dress like a Nancy Meyers character. She nailed the look as early as 1995, when she attended a beachside soirée in an airy button-down, gingham capri pants, and a wide-brimmed sun hat.
Angelina Jolie's Hamptons Outfit in 2005
In the early 2000s, Angelina Jolie ran in the same Hamptons circles as Stewart. She also shared the lifestyle mogul's affinity for lightweight, elevated basics like neutral skirt sets. In Aug. 2005, the Jolie brushed elbows with Meryl Streep and Lindsay Lohan at a star-studded benefit. She arrived in a white tank top, a matching midi skirt, and a beige poncho draped around her shoulders.
Sarah Jessica Parker's Hamptons Outfit in 2015
Sarah Jessica Parker's Hamptons style is still evolving after 20 years of seaside vacations. She always saves a spot for white button-downs in her suitcase, though. In 2015, the Sex and the City star styled one with light-wash skinny jeans and strawberry red sandals. She Carrie-ified the denim outfit with chunky beaded necklaces, a trend that returned for Summer 2026.
Bella Hadid's Hamptons Outfit in 2022
In 2022, Bella Hadid traded hours in NYC traffic for a private helicopter ride straight to her Hamptons hotel. She wore her summer whites while en route, beginning with a lace-trimmed little white dress, matching soft loafers, and a statement headband. Louis Vuitton's bottomless duffle bag became her carry-on.
Dakota Fanning's Hamptons Outfit in 2024
As soon as butter yellow melted onto Spring 2024 runways, stars like Dakota Fanning spread it across their Hamptons' closets, too. The All Her Fault actor chose a buttery summer dress from Zimmermann, which featured scalloped edges and slim waist cut-outs. She shade-matched its faded sunshine shade to peep-toe mules.
Jennifer Lopez's Hamptons Vacation Outfit in 2024
Jennifer Lopez's $10 million Hamptons house in Water Mill is worthy of her rarest Hermès investment pieces. In 2024, she brought her five-figure, Kelly Raffia Picnic Bag out of storage for a downtown shopping day. She paired its chestnut-tinted flap and woven, trapezoidal body with flared jeans, a cotton poplin blouse, and platform espadrille wedge sandals from Gucci.
Gabrielle Union Wade's Hamptons Outfit in 2025
Gabrielle Union Wade and Dwyane Wade have dominated the city's couple style circuit since 2010. Last summer, they matched each other's energy in lightweight daytime looks at Amazon's end-of-summer party.
Union sourced Meghan Markle-approved designer Johanna Ortiz for a black-and-white, hibiscus-printed maxi dress, complete with a plunge halter neck. Her husband, on the other hand, selected a polo shirt and drawstring pants from the brighter section of his personal color wheel.
Julianne Moore's Hamptons Outfit in 2025
Net-a-Porter also hosted a 2025 Hamptons affair for its celebrity clientele. Julianne Moore RSVP'd "yes," but ditched the summer whites dress code for a leather, balloon-like LBD and dad sandals from Khaite. To make the shade decidedly seasonal, Moore carried a fishnet-type tote bag in lieu of a compact evening clutch.
