Olivia Wilde probably didn’t predict the rollercoaster year she’s had with a child custody case involving ex-fiancé Jason Sudeikis, a split with boyfriend Harry Styles, and ongoing headlines about multiple feuds on the set of her film, Don’t Worry Darling. Throughout all of the craziness, the 38-year-old director persevered through fashion. She made bold, creative choices that were the talk of the town. Instead of sitting down for endless interviews, she let her clothing tell a story on the red carpet — and we love her for that.

The mother of two has worked with stylist Karla Welch for over a decade, and together, they’re constantly changing up Wilde’s style. The latest major evolution came with the end of her Booksmart era into her Don’t Worry Darling generation — she went from boho chic to powerfully sleek. (And maybe a bit of Styles’ fashion influence seeped in — how could it not?)

Wilde has joked about her fashion sense being rooted in “a teenager from the early aughts.” She noted to InStyle, “My most comfortable state is when I’m wearing low-rise jeans, sneakers, and a sweatshirt,” she said. “In that, I am unstoppable. And if I’m in a high-waist jean, I can’t let my gut expand.” Now that she’s taken control of her career and become a force to be reckoned with as a director, her fashion has reflected her distinctive style choices this year.

“Directing a movie is the most badass thing I’ve ever done because it is the scariest thing I’ve done,” Wilde continued. “It forced me to tap into my inner strength, and you know what? That may be the most badass thing of all.” See the “badass” fashion decisions Wilde made over the past few years because she knows how to turn heads and start a conversation with her daring ensembles.

A version of this article was originally published on Dec 2022.

Olivia Wilde looked like an Egyptian goddess at the 2023 Met Gala in this white and gold custom Chloé gown

Olivia Wilde was the definition of chic at the inaugural Fashion Trust U.S. Awards on March 21, arriving in an all-black Chloe ensemble that fans adored.

At the 2023 Vanity Fair Oscar Party, Olivia Wilde turned heads in this in this sexy, monochromatic look from Gabriela Hearst that took the naked dress trend to a whole new level.

Olivia Wilde embodied dark gothic vibes yet again in this oversized black blazer with a flower detail on the lapel with a ruffled sheer skirt underneath at the Babylon premiere on Dec 15. Wilde then paired the look with a signature black smokey eye and nude lips.

Just off her breakup with Harry Styles, many headlines shouted that this was Olivia’s “revenge dress,” but her stylist shot down that idea saying on her Instagram Story, “What’s revenge? We dress for the f**king matriarchy.” Nailed it. Women dress for themselves, not for the approval of men.

Olivia showed up at the People’s Choice Awards looking strong and confident in a sheer black dress from Dior’s resort 2023 collection. It has the soft lace to make it feminine with a statement belt that gives it the perfect edge. Bravo!

This Gabriela Hearst might not be for everyone, but Olivia is showing how she’s willing to explore different silhouettes with her red-carpet looks. The corset-like design is structural and sculptural — she definitely took a risk here.

We don’t get to see a ball gown from Olivia very often, but this Erdem dress with tons of tulle is a total fashion moment.

Olivia favors a skirt with billowing fabric, but it’s the minimalist bandeau top that makes the Magda Butrym outfit.

Stepping out of her black dress comfort zone, Olivia wore a striking purple-and-silver chevron gown by Gucci, paired with red opera gloves and heels. It’s a winner!

The conversation piece of this ensemble comes in the top half of Saint Laurent’s spring 2023 collection design. The hood and the cutout in the center showed off her toned abs and took inspiration from the legendary choreographer. Martha Graham.

You can never go wrong in Vera Wang, but we love how the voluminous skirt complements the tiny triangular top revealing just the right amount of decolletage.

Olivia turned heads at the 2nd Annual Academy Museum Gala wearing a sheer nude Alexandre Vauthier with no bra underneath. It seemed like she was standing in solidarity with Florence Pugh’s free-the-nipple-in-fashion moment.

Not only does Olivia love a plunging V-neckline, but she also loves a sexy cutout. This white Stella McCartney dress, for her appearance on The Late Show With Stephen Colbert, is an absolute dream.

Olivia had a solo moment representing Don’t Worry Darling at the film’s premiere at the 70th San Sebastian International Film Festival — and she did not disappoint in a sparkling emerald-green gown by Valentino.

Olivia looked like she just stepped off the Mad Men set in a Kwaidan Editions creation with a high neckline and floral print — it’s a groovy look.

After all of the Don’t Worry Darling headlines, Olivia couldn’t show up in just any dress. She chose a custom gown created by Gucci paired with dazzling diamonds from the designer’s Hortus Deliciarum collection.

Usually, when celebrities make a talk show appearance, they keep their outfit casual, but not Olivia Wilde. She went full glam in a rocking red dress from Dior’s resort 2023 collection on The Kelly Clarkson Show.

A classic green Chanel outfit gets turned upside down with an open jacket and a black bra peeping through at the Venice Film Festival.

Olivia crushed this look that might have been style inspo from then-boyfriend Harry Styles — a blue velvet pantsuit with hot-pink heels. This boss style was much-needed because this was the day she was served child custody papers onstage at Cinema Con.

Olivia knows a power suit when she sees one, and this gorgeously tailored butter-yellow outfit — with a matching purse — hits all of the right notes.

This black-sequin gown is unlike anything Olivia has worn in the past few years — a form-fitting design with a ton of splash, thanks to the hot-pink butterfly.

Olivia looks like she popped off the cover of a romance novel in this flowing Fendi gown at the 2020 Film Independent Spirit Awards in February 2020.

Olivia’s silky floral maxi dress is soft and feminine but, she stepped up the look with a burgundy fringe bag that is the focal point of the outfit.

Not everyone can pull off this color, but Olivia did it magnificently in this Valentino dress with a conservative V-neck (we mean conservative for her tastes) at the 25th Annual Axelle/Bauer-Griffin / Contributor.

Olivia knew exactly what she was doing in this custom-made Etro gold dress with a pop of color in the emerald-stone necklace at the 3rd Annual Hollywood Critics Awards in January 2020.