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26 of the most daring outfits Olivia Wilde has ever worn, from see-through dresses to plunging necklines

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Three photos of Olivia Wilde.

  • Olivia Wilde isn’t afraid to wear daring red-carpet looks.
  • She has worn suits with no shirts, dresses with low necklines, and sheer fabrics.
  • After the 2023 Met Gala, she wore a dress completely covered in cutouts.

Olivia Wilde has been embracing daring fashion for years, as she showed with a black dress in 2006.

Wilde arrived at the 2006 Christopher Reeve Foundation Annual Gala in a form-fitting, sleeveless dress.

The gown had a high neckline with a sheer, illusion bodice that dipped all the way to her navel, which complemented a slit on the skirt.

She continued her streak of see-through black dresses at the 2009 Environmental Media Awards.

Wilde arrived at the awards ceremony in a Stella McCartney cocktail dress.

The short-sleeve dress had a simple, form-fitting skirt, while the scoop-neck bodice had diagonal cutouts made of sheer fabric embroidered with black flowers.

Wilde wore an updo to complete the look.

Wilde’s dress for the 2009 Emmy Awards had a plunging, asymmetrical neckline.

Wilde‘s Marchesa dress had a mermaid skirt made up of tiers of fabric.

The entire dress was covered in applique flowers, and the sweetheart neckline dipped to her stomach and curved around to her hip.

At the 2010 Golden Globe Awards, Wilde sparkled in a low-cut gown.

The Gucci dress appeared to be made of sparkly chain mail that glittered as Wilde walked the red carpet.

The slinky gown had a low-cut, ruched neckline and a flowy skirt.

Wilde stunned in another sheer, black look at the UK premiere of “Cowboys & Aliens” in 2011.

The base of Wilde’s Gucci gown had a sleeveless, black bodice and an A-line skirt with a sheer polka-dot overlay covering the whole dress, as well as her arms.

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The bodice only covered the center of Wilde’s torso, exposing the sides of her chest beneath the overlay.

A collared neckline and faux white tie completed the sexy yet professional ensemble, which Wilde paired with a half-up beehive and a headband.

She rocked a white two-piece for the 2013 Met Gala.

Wilde’s Calvin Klein look consisted of a tube top and a column skirt with a thick belt.

A slit in the skirt broke up the monochromatic ensemble.

Wilde turned heads in a black suit with no shirt at the premiere of “Rush” in 2013.

She arrived in a black two-piece suit, which consisted of a jacket and tapered pants.

The single-button suit showed off her chest and stomach. Black pumps completed the look.

Wilde’s dress for the 2014 premiere of “Horrible Bosses 2” had a daring cutout.

The one-shoulder Michael Kors dress had a cutout on the bodice, creating an asymmetrical look.

A simple, column skirt offset the geometric top.

The top of Wilde’s dress for the 2015 premiere of “Meadowland” looked like a red flower.

The bodice of the Rosie Assoulin dress formed a red flower, with the petals creating cutouts along Wilde’s stomach.

The tea-length skirt was white, aside from one red flower at the hem that tied the look together. Wilde paired the dress with red shoes.

For another “Meadowland” event, Wilde wore a top with a plunging neckline and cutouts.

Wilde kept her look casual with black trousers and a black top.

The shirt had a metallic look to it and was covered in small, square cutouts. The top plunged into a deep V in the middle.

Wilde’s pleated dress for the 2016 Academy Awards had cutouts on the bodice.

The square neckline of Wilde’s cream Valentino Haute Couture dress plunged to her waist, where it flowed out to a full skirt.

The dress was also backless, making the daring bodice even wilder. The pleated fabric gave the gown a timeless feel.

Her long-sleeve dress for the 2016 CFDA Fashion Awards had bodice cutouts.

The Rosie Assoulin had a form-fitting bodice and long skirt.

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Two cutouts on the bodice broke up the fabric and accentuated Wilde’s pregnancy bump.

Wilde shined at the 2018 Vanity Fair Oscars after-party in a dress with cutouts.

The Roberto Cavalli gown had crisscross straps and side cutouts that formed a point at her chest. Sparkles made up the entire dress, which featured a short train that gathered around Wilde’s feet.

The neckline of Wilde’s black dress for the Toronto premiere of “Life Itself” dipped all the way to her navel.

The black, long-sleeve dress had an A-line skirt, which cinched with a gold belt.

The deep-V neckline dipped all the way to the belt.

The star spiced up a red, silk suit with an exposed bra in 2018.

Wilde attended the 2018 GQ Men of the Year Party in a red, silk Selmacilek suit.

She left the jacket open with no shirt, showing off a red, lace bra.

She showed off her love of suits sans shirts at an event for Audi in 2021.

Wilde’s Kwaidan Editions jacket had pointed shoulder caps and a single black button.

The coordinating pants flared out, giving the colorful look a modern feel.

She rocked another suit at a Variety party in 2022.

At a party ahead of the Venice Film Festival, Wilde wore an oversized black jacket and coordinating, tapered pants.

The jacket buttoned at Wilde’s navel, exposing almost her entire chest.

Wilde wore another no-shirt look at a “Don’t Worry Darling” event in 2022.

At a photo-call for the Venice Film Festival, Wilde arrived in a green Chanel jacket and coordinating skirt with buttons lining the center.

She wore no shirt under the jacket, opting for a black bra instead. Knee-high, black boots completed the ensemble.

Wilde wore a bold Gucci dress to the premiere of “Don’t Worry Darling” at the Venice Film Festival in 2022.

The ball gown was made of billowing yellow fabric, and its capped sleeves flowed into a cape with a ruffled hem.

The neckline dipped to Wilde’s midriff, and the bodice was accented by sparkly detailing that framed Wilde’s figure.

A few weeks later, Wilde wore a backless green dress to the San Sebastian International Film Festival.

Wilde arrived at the festival in a skin-tight Valentino gown that flowed into a trumpet skirt.

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The sparkly, green gown had a halter neckline with long ties in the back.

Wilde wore another dress with a low neckline at the 2022 ELLE Women in Hollywood Celebration.

The bodice of the star’s Vera Wang dress was barely there, as it consisted of spaghetti straps and very little fabric covering Wilde’s chest.

A poofy, tea-length skirt contrasted the minimalist top.

Wilde wore a completely see-through dress in October 2022.

Wilde arrived at the event in a long-sleeve, form-fitting dress from Alexandre Vauthier.

The dress was made of a sparkly, silver fabric that looked like chain mail, and the trim was lined with pink feathers.

The entire gown was see-through. You could see the outline of Wilde’s underwear through the gown, and she didn’t wear a bra with the daring look.

Wilde wore a bandeau to the the Baby2Baby Gala in November 2022.

Wilde paired the tiny top with a full skirt from Magda Butrym that cost $3,140, according to People.

The skirt was high-waisted, and it had pockets. Gold, drop earrings completed the look.

Wilde donned a sheer, lacy dress for the People’s Choice Awards in December 2022.

Dior designed the dress for its 2023 Resort collection, according to Women’s Wear Daily.

The black dress was almost entirely see-through, and it was covered in a delicate floral pattern, showing the high-waisted, black underwear Wilde wore beneath the gown.

She added a chunky belt to the bold ensemble.

Wilde’s dress for the Vanity Fair Oscars after-party was designed to show off her bra..

Wilde attended the after-party in a white gown designed by Gabriela Hearst.

The asymmetrical dress had one long sleeve, and the neckline curved from her shoulder to her hip, leaving her chest bare aside from her black bra.

Sparkly jewelry completed the ensemble.

Wilde wore a dress covered in cutouts after the 2023 Met Gala.

The silver sheath dress was made of a netted material, so the entire gown was covered in cutouts, revealing Wilde’s underwear.

Platform boots and a gold purse completed the outfit.