Olivia Wilde is the ultimate cool girl and her fashion game just keeps leveling up.
Though the superstar has been forced to endure preying eyes into her personal life over the past few years, throughout all of the craziness, the 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.
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Breakthrough Prize Ceremony (2024)
Image Credit: Photo by JC Olivera/WireImage. At the 10th Annual Breakthrough Prize Ceremony, Olivia Wilde looked so stunning in this cutout monochromatic dress.
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Oscars After Party (2024)
Image Credit: Christopher Polk/Variety via Getty Images Wilde showed off her classic cool girl style with a simple black gown and undone hair at the 2024 Vanity Fair Oscar Party.
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Oscars Pre-Party (2024)
Image Credit: Getty. Olivia Wilde rocked an ultra-daring sheer black dress.
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Polka Dotted Power (2023)
Image Credit: Photo by Stefanie Keenan/Getty Images for Baby2Baby. Olivia Wilde looked so stunning in this monochromatic, polka-dotted dress from Balmain for the Baby2Baby Gala in 2023.
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Dark Suitted Up (2023)
Image Credit: Photo by Stefanie Keenan/Getty Images for Neiman Marcus. Olivia Wilde turned heads in this black pinstriped Schiaparelli suit for the Neiman Marcus Welcomes Schiaparelli’s Daniel Roseberry event!
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Fantastic in Faux Fur (2023)
Image Credit: Photo by Stephane Cardinale - Corbis/Corbis via Getty Images. For Paris Fashion Week, Olivia Wilde rocked a daring look of a faux fur, floor-length jacket, along with heeled combat boots, and her usual black and white clothes udnerneath.
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Daring Suit (2023)
Image Credit: Photo by Raymond Hall/GC Images. For the Kering Caring for Women Dinner on Sept 12, 2023, Olivia Wilde rocked a daring black suit look comprised of silky slacks and a matching jacket, along with a black bra as a top.
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Egyptian Princess at the Met (2023)
Image Credit: Michael Buckner for Variety Olivia Wilde looked like an Egyptian goddess at the 2023 Met Gala in this white and gold custom Chloé gown
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Gothic Gal Returns (2023)
Image Credit: Photo by Gilbert Flores/WWD via Getty Images. 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.
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New Take on the Naked Dress (2023)
Image Credit: Photo by Alberto Rodriguez/Variety via Getty Images. 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.
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A Blazer With a Twist
Image Credit: Getty Images 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.
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Not a Revenge Dress
Image Credit: Axelle/Bauer-Griffin/FilmMagic. 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!
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It’s High Art
Image Credit: Michael Tullberg/FilmMagic. 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.
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Soft & Pretty
Image Credit: Jon Kopaloff/Getty Images. 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.
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Tiny Top
Image Credit: Araya Doheny/Getty Images for Baby2Baby. Olivia favors a skirt with billowing fabric, but it’s the minimalist bandeau top that makes the Magda Butrym outfit.
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Bold Color Choice
Image Credit: Axelle/Bauer-Griffin/FilmMagic. 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!
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Inspired by Martha Graham
Image Credit: Jon Kopaloff/Getty Images for Max Mara. 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.
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A Twist on a Classic
Image Credit: Kevin Winter/Getty Images. 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.
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Free the Nipple
Image Credit: Axelle/Bauer-Griffin/FilmMagic. 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.
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Crazy Cutouts
Image Credit: Raymond Hall/GC Images. 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.
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Emerald City
Image Credit: Carlos Alvarez/Getty Images. 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.
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Throwback Design
Image Credit: JB Lacroix/Getty Images. 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.
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The Moment
Image Credit: John Phillips/Getty Images. 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.
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A Star Entrance
Image Credit: NBCUniversal/Getty Images. 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.
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Make It Chanel
Image Credit: Eli Villa/Getty Images. A classic green Chanel outfit gets turned upside down with an open jacket and a black bra peeping through at the Venice Film Festival.
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Drama for Days
Image Credit: Gabe Ginsberg 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.
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Monochromatic Bliss
Image Credit: Stefanie Keenan / Contributor 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.
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Butterfly Fashion
Image Credit: Axelle/Bauer-Griffin / Contributor 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.
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Romantic Red Carpet
Image Credit: Albert L. Ortega 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.
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Next-Level Accessory
Image Credit: Araya Doheny / Contributor 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.
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Confident in Coral
Image Credit: Axelle/Bauer-Griffin / Contributor 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.
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Glowing in Gold
Image Credit: Rachel Luna 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.
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