While casual fans of Bessette-Kennedy’s style might imagine her wardrobe as simple above all else, the fashion insider had a taste for the out-there stuff, too. Case in point: this gala ensemble, which includes pieces from the avant-garde labels Yohji Yamamoto and Comme des Garçons. You don’t need to wear statement ruffles to achieve the same sense of cool, but you should be open to taking some swings. Why not a gathered blouse tucked into smart trousers to start?
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Bring it into 2026 by adding statement earrings, a metal cuff bracelet, or a bold brooch. Sculptural jewelry is trending for spring, and it’ll add additional texture while echoing the metallic sandals.
8. Khaki skirt + brown boots
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