Jackie Kennedy's Iconic New England 'Fits Should Be Your Summer Style Inspo

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Jackie Kennedy could nail coastal elegance like no other. She wore outfits that had a touch of preppy flair, matched with a European sophistication that still — to this day — proves inspirational. Jackie spent a lot of time in New England; as a child, she summered in Newport, Rhode Island, and later, because of President John F. Kennedy's family home in Hyannis Port, Massachusetts, Jackie spent a lot of time at the Kennedy compound. Thus, New England — and its distinct aesthetic — was familiar territory.

New England fashion has long been defined by its quiet luxury and old-money aesthetics, made up of understated elegance through maritime navy looks, Breton stripes, and natural fibers. It's not an overly flashy style because, at its core, the New England aesthetic is meant to be functional and outdoorsy — It's ideal for women who want to look good going from the garden to a boat. While Jackie could nail a sumptuous gown in the Washington D.C. landscape, her style in New England summers was subdued and relaxed, and she embraced the chic utilitarian styles that make New England style so elegant. She sported straw sun hats, jaunty summer shorts, and simple sundresses that were so timeless, they're still perfect warm-weather outfits by today's fashion standards.

During the summer of 1953, right before Jacqueline Bouvier married John F. Kennedy, she spent time at the Kennedy compound in Hyannis Port, Massachusetts. They would go on to get married in September of that year in Newport, Rhode Island. During this particular visit, Jackie wore a checkered sleeveless top with high-waisted shorts and a wide-brimmed sun hat. The casually chic fit was the perfect outfit for a warm day on the coast. Recreate it with a Dookttker sleeveless gingham blouse and a pair of tan Belle Poque Bermuda Shorts. 

In July 1960, Jackie Kennedy and John F. Kennedy sat on a sun chair to read a book with their daughter, Caroline Kennedy, at Hyannis Port, Massachusetts. The perfect family picture also captured Jackie's flawless grasp of New England style. Her cheerful, floral summer dress was simple and elegant, modest and breezy. Copy Jackie's look with a Belle Poque Floral Dress or this square neck Sureple midi dress with blue and red flowers for that New England charm. 

Jackie Kennedy was the queen of the shift dress, and the summer staple still counts as a key example of trends from the '60s that are perfect for older women. Quite frankly, women of any age look great in shift dresses, and Jackie was a prime example of that. In 1970, she walked with her sister, Princess Lee Radziwill, rocking a short, white shift dress, kitten heels, and a black coat draped over her shoulders. This classic influence is still undeniably present today.

Jackie Kennedy's ultimate New England accessory was the head scarf. While out boating, she often pulled her hair back using a simple scarf, securing it behind her head at the nape of her neck. Fortunately, head scarves are high on the list of accessory trends that will elevate your summer 2026 outfits, so Jackie's favorite accessory is very much in style again. Mimic her simple look with this cream MEISEE mulberry silk scarf from Amazon, or opt for more color with this equestrian-inspired silk scarf. 

Breton stripes are timeless and charming. The nautical design with blue and white horizontal lines is historically French, but fits in well with New England's maritime aesthetic, and Jackie Kennedy knew that. She wore a simple striped shirt with oversized sunglasses in 1976, offering up easy, summer styling. Capture this vibe with a BTFBM crew neck blue and white striped shirt, or get a little more creative with a V-neck boater shirt with navy trim. Finish it off with a pair of oversized sunglasses to really get it right. 

Jackie Kennedy knew how to rock a pair of fitted white capris. On a barefoot outing with her children, she styled her crisp trousers with a black T-shirt and her iconic sunglasses, creating a capsule outfit that could easily serve as a summer staple. The bottoms were favored by her contemporary, Audrey Hepburn, as well. Hepburn's most iconic outfits are still so chic today, and capris were a mainstay of her wardrobe. If both style mavens loved them, it's worth getting a pair.

In true New England maritime style, Jackie Kennedy frequently wore boatneck dresses. This particular style features a horizontal neckline that runs across the clavicle and extends to the tips of the shoulders. In the photo above, Jackie wore a brocade, belted shift dress with the coveted boat neck, serving up a dressed-up summer silhouette. Get Jackie's look with a tweed, pink sheath dress featuring the iconic neckline. Her little white gloves were a nice touch. 

While she was technically in New York City this day in 1970, Jackie Kennedy showed us that her street style had a preppy jolt of New England flair. Part of its charm was that her outfit was so simple. She styled a fitted, navy button-down shirt with straight-leg pants, and her finishing touches were so distinctly Jackie: a long strand of pearls and her big sunglasses. It's a delightfully easy look to recreate, too. Grab a fitted, navy button-down and pair it with straight-leg navy dress pants. Pearls would be a nice touch. 

Sometimes, a New England summer calls for a refined dress code. Jackie Kennedy showed us just how to do this while posing with John F. Kennedy and their daughter, Caroline, in 1960. She wore a pink gingham dress with a white necklace and a bracelet, capturing a more traditional element of coastal style. Best of all, it's easy to replicate. Style a pink gingham dress with a necklace, or pay homage to Jackie's inspiration with a more modern, flirty interpretation, like this pink gingham V-neck dress.