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Dressed-Up Shirting
When it came to elevating classic pieces, few could compete with Bessette-Kennedy. For a black-tie gala at the Whitney Museum of American Art, she transformed a white button-down into an eveningwear essential, unbuttoning it to the breastbone, rolling up the sleeves and adding a floor-skimming tiered skirt. Accessorised with black sandals and a gold beaded bag, the look was the epitome of uptown glamour without compromising her pared-back aesthetic. For similar semi-formal soirées, channel the look in a relaxed Nili Lotan button up and Acler’s maxi skirt.
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Naked Sandals
This must-have shoe was a favourite of Bessette-Kennedy’s. The insouciant ease of a thin-strapped, minimal mid-heel works just as well with denim as it does with a dress. Look to Totême for inspiration.
Ron Galella
A Form-Fitting LBD
Evening gowns don’t get more classic than form-fitting black. Bessette-Kennedy wore hers with elbow-length gloves and pointed stilettos to elevate the simple design, yet kept her hair relaxed in a loose chignon. We love this similar style from Matteau.
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The Power Headband
Hair accessories have been back–and bigger than ever–for a while, but Bessette-Kennedy was an early advocate of the more minimalist take, regularly pairing a broad tortoiseshell headband with oval shades and a white T-shirt.
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The Slinky Slip
Bias-cut slips formed the backbone of Bessette-Kennedy’s wardrobe, from her Narciso Rodriguez wedding gown to black mini dresses worn during blistering summers in the city and ribbed grey styles hidden under cover-ups on cooler days.
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Beige and Black
Once dismissed as an unwearable combination, Bessette-Kennedy was a long-time champion of beige and black in all its forms: a pale fawn pencil skirt with a black knit and brown boots; a black T-shirt with camel-hued trousers and loafers; dark caramel cords with a black turtleneck.
Jeff Kravitz
A Slick of Red Lipstick
Bessette-Kennedy’s beauty looks were like her outfits: simple, yet effective. When she did amp things up with red lipstick, her preference was a rich hue apparently applied with her ring finger, to achieve a “bled” effect. Follow suit by adding a just-kissed red pout to a sheer base and a slick of mascara.
Brooks Kraft
A Chiffon Detail
A little black dress doesn’t have to be plain. When in search of a stand-out detail, Bessette-Kennedy preferred to play with texture, rather than print–as evidenced by this tulle overlay.
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The Bandana
Much like her mother-in-law Jacqueline Kennedy, who often covered her hair with loosely-tied silk scarves while on holiday in Capri, Bessette-Kennedy had a penchant for block-color bandanas. Paired with denim, a tank, and a longline blazer, it’s the ultimate in city-appropriate Riviera chic.
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The Floral Midi Dress
Bessette-Kennedy knew how to turn up the volume on a floaty summer frock: just add stilettos, bed-head hair and a black patent bag for off-duty style that’s equal parts polished and effortlessly cool. Hunt down the perfect floral midi dress and combine it with shiny accessories that lend an edge.