Olivia Wilde Frees the Nipple at Fashion Week

Olivia Wilde‘s latest look left little to the imagination.

The Don’t Worry Darling director stepped out in Manhattan during New York Fashion Week Sept. 11 wearing a sheer top with no bra, paired with a long black skirt and matching coat, which at one point, the wind blew to the side to reveal her right nipple.

After wearing the daring ensemble to the Michael Kors Collection spring/summer 2026 runway show at Terminal Warehouse, Wilde changed into a semi-sheer, frilly white maxi dress to attend W magazine and Bloomingdale’s New York Fashion Week celebration at Eleven Madison Park Restaurant.

And this isn’t the first time The O.C. alum has taken risks name of fashion. Indeed, the 41-year-old has stepped out in sheer, bra-less looks before, including at Saint Laurent’s presentation at Paris Fashion Week in February 2024 and at the Vanity Fair 2025 Oscars after-party this past March. She has also posed nude before, appearing naked in a 2021 True Botanicals campaign.

Wilde showcased her latest daring fashion styles one week after she was photographed packing on the PDA with Caspar Jopling, whose divorce from Ellie Goulding—with whom he shares son Arthur, 4—was finalized earlier this year.