Olivia Wilde’s Plunging Suit At Milan Fashion Week Was Positively Sleek

Would you believe fashion month is already halfway through? After a buzzy New York Fashion Week and a nipply London leg, Milan kicked off the Italian segment to fashion frenzy. Demna’s hotly anticipated debut for Gucci, for example, caused quite a stir, especially since he eschewed the brand’s traditional fashion show format for a short film premiere. (And the clothes? Well, expect a Gucci renaissance.)

Another event that made waves was Tiffany & Co.’s party. To celebrate its new high jewelry collection, the label gathered some of fashion’s brightest to wear equally sparkly bling. Out of the many attendees who dazzled, Olivia Wilde ultimately stood out, both for her diamonds and daring ensemble.

Olivia’s 22-Carat Diamond Jewelry

The jeweler’s clientele helped welcome the fall collection, Blue Book 2025: Sea of Wonder, which featured diamond-clad pieces inspired by the ocean’s inhabitants and mainstays. Sea horses, turtles, urchins, flora, and anchors lined sparkly necklaces, earrings, and rings. Designed by Nathalie Verdeille, the label’s chief artistic officer, each aquatic theme highlighted a different color palette or gemstone.

One of the first to get a hold of the designs, Wilde wore several pieces from the glitzy collection, the highlights of her look. The Don’t Worry Darling director wore a statement two-toned necklace with over eight carats of diamonds. She also donned two rings: an urchin-inspired one with over nine carats of diamonds, and another with over five. That brought her total sparklers to a whopping 22 carats.

Her Cleavage-Baring Plunging Look

While the sparklers were definitely scene-stealing, her all-black outfit also deserved applause. The Booksmart director wore a shiny blazer with boxy shoulders, one side of which was affixed with a massive Carrie Bradshaw-esque rosette. Ever the risqué dresser, Wilde styled it sans top and bra, leaving her décolletage exposed. She also left a button undone for a sliver of midriff.

For an edgy, cool-girl twist, she paired the jacket with a leather maxi skirt pulled low on her hips and pointy pumps.

A dazzling serve.