How does the fashion cognoscenti mentally prepare for a big gala? By attending a chic pre-gala dinner, of course. On Friday, Oct. 17, ahead of the Academy Museum Gala, W Magazine’s editor-in-chief, Sara Moonves, and Chloé’s creative director, Chemena Kamali, rounded up some of the chicest style stars at Los Angeles hotspot La Dolce Vita.
The intimate dining event’s guest list included Addison Rae, sisters Elle and Dakota Fanning, Maya Rudolph, and Leslie Bibb, among other stylish attendees. The one style icon, however, whose look now lives rent-free in my mind is Olivia Wilde.
Olivia’s Updated Suiting
Wilde’s style DNA is singularly defined. The Don’t Worry Darling director typically opts for the flowiest, dreamiest pieces that embody her spicy, free-spirited ethos. She switched it up at the dinner, however, with something more tailored.
A take on “suiting,” she wore a black cropped tuxedo blazer with boxy power shoulders and paired it with a matching pleated maxi skirt with a three-buckle detail. As for her top, she layered a cream ribbed knit sweater, unbuttoned nearly all the way down to her waist over a slinky beige slip, with sheer lace panels and a décolletage-baring neckline. She accessorized the look with a two-pendant necklace looped twice around her neck and draped lariat-style, and completed it with boot clogs.
The pièce de résistance? Her arm candy. Fashion girls can clock the padlock hardware on the bag, the signature emblem of the Chloé Paddington. The bag, originally designed by Phoebe Philo in 2005, was a noughties staple, slung by the decade’s it girls like Kate Moss and Sienna Miller. Kamali, expertly leaning into early aughts nostalgia, reimagined the Y2K must-have and debuted it via her Fall/Winter 2025 Paris Fashion Week show, before it officially launched in September.
Unsurprisingly, the ever-fashion-forward Wilde already got her hands on the bag. Her choice: a caramel brown colorway.
Getty Images for W Magazine
Her Gala Look
She channeled a similarly boxy look at the gala proper. Her floor-length Saint Laurent gown, which was loose on top and more fitted from the hips down, featured powerful, angular shoulders, a mock neck, and long sleeves.
Emma McIntyre/Oscars/Getty Images Entertainment/Getty Images
Back-to-back slays.
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