Celebrity Style

Olivia Wilde’s Plunging Dress Was Uncharacteristically Maximalist

The bedazzled gown also flaunted major side boob.

by Alyssa Lapid
Olivia Wilde at Michael Kors RTW Spring 2025 as part of New York Ready to Wear Fashion Week held at ...
Gilbert Flores/WWD/Getty Images

Olivia Wilde may have gotten her start as an actor on The O.C., but these days, she’s more focused on directing — and empowering fellow women filmmakers.

On Tuesday, Sept. 17, the Don’t Worry Darling director attended the kickoff luncheon of Through Her Lens. Hosted by Chanel and Tribeca Enterprises, the annual mentorship initiative selects 10 emerging female filmmakers to mentor closely in a three-day program. The event culminates in a competition: participants partner up to pitch their film ideas to a jury. One winner is awarded full funding while the rest receive partial grants.

Wilde took a more active role than chic guest, of course. She also sat on the five-member jury, which included Hollywood powerhouses Lucy Liu, Joanna Calo, Beanie Feldstein, and Da’Vine Joy Randolph. On Thursday, Sept. 19, participants, jurors, and other guests gathered for the final program cocktail, where the winners were announced. Naturally, Wilde bookended the yearly event in two stylish numbers — one especially spicy.

Olivia’s First Look: A Tweed Pantsuit

At the kickoff luncheon, held in New York, Wilde was all business in a Chanel tweed pantsuit. She added a retro twist with her ’70s-inspired styling, and left her jacket open to reveal an abstract top and paired it with floor-length wide-leg trousers.

Joe Schildhorn/BFA.com

Her Party Look: Totally Plunging

Her party look on Thursday was the total sartorial opposite. She went from all business to NSFW. The Booksmart director wore a dress with slinky spaghetti straps and a deep, plunging neckline — one that dipped past her breasts in the front and on the side.

The drop-waist dress also featured a fitted bodice and an A-line skirt.

Dimitrios Kambouris/WireImage/Getty Images

Wilde is minimalist at heart and is rarely seen in prints, patterns, or anything remotely OTT. (Her off-duty uniform is a sports bra.) She dressed up for the occasion and veered from her usual style MO. Her choice of LBD — little blue dress — was crystal-encrusted, floral, and featured see-through eyelet holes all over.

Dimitrios Kambouris/WireImage/Getty Images

She completed the look with a yassified Chanel classic: two-toned slingbacks with a shimmery twist. Everything else was kept effortless including her simple jewelry, messy tousled waves, and barely there makeup.

Dimitrios Kambouris/WireImage/Getty Images

Two chic numbers.