It’s no secret that Olivia Wilde is one of the most fashionable talents in Hollywood – and that includes some fierce braless looks on the red carpet! The Don’t Worry Darling director always looks flawless when she’s stepping out at an event, but in her everyday life, she prefers a more casual approach.
“I’m still pretending to be a teenager from the early aughts. My most comfortable state is when I’m wearing low-rise jeans, sneakers and a sweatshirt,” Olivia, who shares kids Otis and Daisy with ex-fiancé Jason Sudeikis, told InStyle in a January 2020 interview. “In that, I am unstoppable. And if I’m in a high-waist jean, I can’t let my gut expand.”
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When Olivia isn’t dressed like her character from The O.C., Alex Kelly, she’s rocking long, flowy dresses — i.e. the floral Gucci number she wore to Jeff Azoff‘s wedding in January 2021 with boyfriend Harry Styles by her side. The actress and the “Fine Line” artist made their debut as a couple at the star-studded affair and have been going strong ever since.
Olivia “is giving this relationship all she can because she truly wants to make it work,” a source previously told In Touch. “However, it is not easy. Olivia and Harry are both working on projects, and Harry has a million things going on. He just wrapped his North American tour and will start on his European tour shortly, so he will be in Europe rehearsing and working on music.”
The New York native “balances her schedule with her children’s, as she has joint custody with their father,” the insider added. “It’s tough for Olivia because in her heart she wants to be with Harry all the time, but it’s just not possible.”
Olivia and Harry began their romance after working on her upcoming film, Don’t Worry Darling. The former One Direction singer plays the male lead, Jack.
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“Harry and Olivia had chemistry almost instantaneously on set. It was only a matter of time before they got together,” a separate source revealed to Us Weekly in January 2021.
As for Olivia and Jason, the former flames, who split in November 2020 after nearly a decade together, are amicable. “They’ve been separated for months now and there really is no drama. They’re handling this like adults,” an additional insider told Us at the time. “It’s all about coparenting their kids, Daisy and Otis. That’s the priority for them.”
Scroll through the gallery below to see photos of Olivia Wilde’s most fashionable braless looks over the years.
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Chelsea Lauren/Shutterstock
Taking the Plunge
The Don’t Worry Darling director donned a plunging black ball gown with tiny spaghetti straps to Elle Women in Hollywood Celebration in October 2022.
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Image Press Agency/NurPhoto/Shutterstock
Nothing Left to the Imagination
Olivia made sure all eyes were on her in a totally see-through Alexandre Vauthier gown at the second annual Academy Museum of Motion Pictures Gala.
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MEGA
Jaw-Dropping!
The O.C. alum donned a super sexy white cut-out dress while leaving an appearance on The Late Show With Stephen Colbert in New York City in September 2022.
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Shutterstock
Green Goddess
The TRON: Legacy star donned a sexy backless sequin halter gown for the Don’t Worry Darling premiere at the 70th San Sebastian International Film Festival in Spain.
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Manuele Mangiarotti/ipa-agency/Shutterstock
Not So Mellow Yellow
Olivia wowed in a canary yellow sleeveless gown with a deep V cut down to her waistline at the Don’t Worry Darling Venice International Film Festival premiere in September 2022.
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MEGA
Fantastic in France
The stunner rocked a very low off-the-shoulder pale green dress with a sheer skirt for a night out in Paris in June 2022.
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Matt Baron/Shutterstock
The Coolest
Olivia looked sexy in this black bustier top.
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Anthony Harvey/Shutterstock
Classy
This Fendi frock with a plunging neckline was a moment.
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Matt Baron/Shutterstock
Lights Up
Olivia’s wardrobe includes a lot of color.
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Mark Von Holden/Invision/AP/Shutterstock
Metallic Queen
The necklace was the real star of the show here … next to Olivia, of course.
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Rob Latour/Shutterstock
Classic Hollywood
Olivia looked flawless in this Ralph Lauren gown.
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Piers Allardyce/Shutterstock
Ethereal
This peach Giambattista Valli ensemble was gorgeous!
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Suzanne Cordeiro/Shutterstock
All About the Sleeves
Olivia loves a dress with fun bell sleeves.
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