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How To Dress Like Carolyn Bessette-Kennedy On Holiday

What makes someone a style icon? Ultimately, it’s someone who shapes fashion through their choice of clothes. They are engaged with fashion, but not dictated by it. Carolyn Bessette Kennedy is a perfect example, a fashion publicist who is back in the public consciousness again this week with the arrival of Ryan Murphy’s new television series, Love Story, about her ill-fated relationship with John F. Kennedy Jr. The original poster girl for quiet luxury, CBK’s restrained, understated look came to epitomise 90s minimalism, and paved the way for contemporary, fuss-free brands such as Khaite, The Row and Toteme. Here, we translate her day-to-day understated, restrained wardrobe into holiday mode, ready for your next trip.

 

The art of Caroline Bessette-Kennedy dressing lies in its simplicity, which is perhaps why her style has been so WIDELY EMULATED in the past few years; it’s easy to deconstruct and recreate. To embrace your inner CBK, think about PURPOSEFUL CLASSICS. She was perhaps the originator of the CAPSULE WARDROBE, an approach that lends itself well to packing (especially as airline luggage restrictions become increasingly miserly). At home in New York, CBK’s look was characterised by polish, on holiday she took a more RELAXED SARTORIAL ALTER-EGO. Summers were spent with the Kennedys in New England, where her style choices had a more BREEZY, PREPPY ENERGY that depended on classic pieces, a neutral colour palette and elegant staples. 

To bring a hint of CBK to your suitcase, pack with intention – there should be no surplus items here (agony for me personally). You’ll need classic pieces that can be worn multiple ways – a white shirt that can be worn as a beach cover-up or tucked into shorts or a pair of straight-leg, cropped jeans; a sweatshirt and a fine cashmere knit for cooler evenings, a low-key summer dress that works for a relaxed lunch and for a more formal dinner, and footwear free of ornamentation – sporty Superga trainers for city strolls, Havianas for the beach and a leather, barely-there pair of thong sandals for the evening. Everything should prove useful. CBK was elegant, but she was also practical; a style lesson in and of itself.

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Lead image: Disney/Hulu

Ella Alexander is Citizen Femme’s fashion features editor. She started her career at the Evening Standard, and has since held senior editorial roles at Vogue, The Independent and Harper’s Bazaar, where she remains a contributing editor. She also writes for The Telegraph, Sunday Times Style, Service95 and CNN. She is an author, having co-written Dame Zandra Rhodes’ memoir, Iconic: My Life In Fashion In 50 Objects, published by Transworld in July 2024. Her favourite travel destination is Catania, Sicily’s second city.

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