4 Summer-Style Icons We’re Planning Our Looks Around This Season  

While we’re happily slipping into the trending tomato reds and lucky charms on offer this season, summer outfitting wouldn’t feel right without a little inspiration from the archives—and this year, our forever-favorite summer-style icons feel more on point than ever. Maybe it’s because popular culture is having a nostalgia moment. Or maybe it’s because revisiting the classics reminds us that even if you can’t drink Hugo spritzes all day or eat soft-serve every night, certain summer traditions never change. 

Jackie O: High Summer in Hyannis Port

There may never be another Camelot, but this season’s oversize sunnies, shapeshifting scarves, and slim strappy sandals make it easier than ever to copy its queen. Signature accessories aside, it’s the dresses—short with clean lines for the Hyannis Port lawn, sweeping silhouettes for events—that made Jackie’s summer style instantly recognizable. If you’re not on a yacht this season, channel her Onassis-era energy in an Emporio Sirenuse caftan designed by another iconic matriarch: Carla Sersale, the woman behind the eponymous Amalfi Coast resort. 

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Gwyneth as Marge Sherwood: Preppy and Polished in Positano

The wardrobe department worked some serious movie magic in this classic: The Talented Mr. Ripley is set in the late 1950s, premiered in 1999, and somehow Marge’s swishy calf-grazing skirt and collared cardigan are all we want to wear this summer—the looks are that timeless. Vintage-inspired details like outsize buttons and shirttail bows deliver just enough whimsy and escapism, so even if you can’t be in Positano, with the right wicker basket you can faux-citano. 

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Carolyn Bessette Kennedy: Hot Girl in the City

The summer of CBK has only just begun, and you have plenty of opportunities ahead to pack your weekender with a cable knit, classic Wayfarers, and a string bikini that feels so ’90s, in the best way. When the daily grind drags you back in on Monday, light up the office hallway in slim-cut capris and the kind of flip-flops that mean business—and catch compliments.

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Jane Birkin: Le Café to La Piscine

When we borrow from Jane, it’s often in broad strokes—more like an exercise in channeling creativity as we craft our own personal style. A breezy babydoll dress is an aesthetic choice, sure, but there’s something about her style that’s completely singular. This is, after all, the woman who walked around Paris with a wicker basket so we could carry a fan-shaped raffia bag to Cove and order the lion’s mane schnitzel. Is Birkin dressing a feeling? Maybe. Is a Breton stripe always a good idea? Definitely.

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