The 21 Best Vanity Fair Oscar Party Fashion Moments of All Time

Kate Hudson, Zoe Kravitz, and Dakota Johnson at the Vanity Fair Oscar Party — Barry King / WireImage / John Shearer / Getty Images / Karwai Tang / Getty Images

For the past nine decades, the Oscars have remained the most celebrated night in Hollywood. Film aficionados watch to see if their favorite films and actors take home a gold statuette, but for fashion people, the real show happens before and after the ceremony. Stars walk the red carpet in designer gowns and suits, but like any good event, the fun really happens at the afterparty. Of course, we’re talking about the Vanity Fair Oscar Party.

Most celebrities flock to the soirée after the Oscars have ended, and some don’t even attend the Oscars at all. For us fashionphiles who didn’t catch an invite, we know that when Monday morning rolls around we will be fed a whole new batch of looks from the big bash. Below, read on for the 21 best fashion moments from the Vanity Fair Oscar Party.

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Kate Hudson (2000)

Kate Hudson at the Vanity Fair Oscar Party in 2000. — Barry King / WireImage

In a true Y2K fashion moment, Kate Hudson wore this gray cutout gown and matching shawl to the 2000’s Vanity Fair party. Her soft glam matched the vibe of the outfit to a T.

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Cher (2000)

Cher at the Vanity Fair Oscar Party in 2000. — Barry King / WireImage

Cher stole the Academy Awards red carpet in 1986 with her iconic "revenge dress," but this Oscar’s after party look from 2000 simply does not get the hype it deserves. The singer and Oscar-winner took a more unconventional route, and wore a Canadian tuxedo complete with embellished jeans and a sequined purple top.

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Madonna (2006)

Madonna at the 2006 Vanity Fair Oscars Party — George Pimentel / WireImage

Who can forget this silky pink Versace dress Madonna wore to the 2006 Vanity Fair party? It was a departure from the singer’s usual aesthetic, down to the bedazzled heels, and it proved the pop culture icon could perfect any style.

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Irina Shayk (2015)

Irina Shayk at the 2015 Vanity Fair Oscar Party — Pascal Le Segretain / Getty Images

In 2015, model Irina Shayk turned heads in a daring sheer paneled Atelier Versace ensemble. She kept the look otherwise simple with black pointed-toe pumps and nude lipstick.

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Taylor Swift (2016)

Taylor Swift at the 2016 Vanity Fair Oscar Party — Pascal Le Segretain / Getty Images

Ahead of her Reputation-era, Swifties were gifted this edgier look from the Grammy-winning singer. The skin-baring Alexandre Vauthier gown was an unexpected choice for the Vanity Fair party, but it paired seamlessly with her freshly cut blunt bob.

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Jessica Alba (2017)

Jessica Alba at the 2017 Vanity Fair Oscars Party — Jon Kopaloff / FilmMagic

Jessica Alba stunned in a delicate baby blue floral dress at the 2017 Vanity Fair Oscar Party. The actress paired the Ralph and Russo number with a metallic clutch and silver platform heels.

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Lupita Nyong'o (2018)

Lupita Nyong'o at the 2018 Vanity Fair Oscar Party — Axelle / Bauer-Griffin / FilmMagic

Lupita Nyong’o changed out of her red-carpet Versace gown and into this beaded gown by Armani Privé for the after party in 2018. She paired the dress with sparkly chandelier earrings.

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Janelle Monáe (2018)

Janelle Monae at the 2018 Vanity Fair Oscar Party — John Shearer / Getty Images

Janelle Monáe always guarantees to bring a show-stopping look to every carpet, which was the case at the 2018 after party. The multi-talented singer wore a structured red Christian Siriano suit with embellished shoulder pads and a dramatic train.

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Zoe Kravitz (2018)

Zoe Kravitz at the 2018 Vanity Fair Oscar Party — John Shearer / Getty Images

Zoe Kravitz has had a few best dressed moments at the Vanity Fair party but this Saint Laurent puffy mini dress is certainly a winner. The feather-detailed mini was a perfect choice for bringing the party to the actual party.

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Jennifer Lopez (2019)

Jennifer Lopez at the 2019 Vanity Fair Oscar Party — Axelle / Bauer-Griffin / FilmMagic

J.Lo switched out of her Tom Ford mirrored red-carpet gown and into this more playful peacock-like Zuhair Murad gown. She also switched up her hair from sleek and straight to more voluminous curls to fit the look.

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Olivia Colman (2019)

Olivia Colman at the 2019 Vanity Fair Oscar Party — John Shearer / Getty Images

Olivia Colman took home the Best Actress Oscar in 2019 for her work in The Favorite, but she also earned best dressed on the Vanity Fair red carpet. After wearing an emerald green gown, the actress changed into a cream 1930s-inspired dress from Stella McCartney.

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Kerry Washington (2020)

Kerry Washington at the 2020 Vanity Fair Oscar party — George Pimentel / Getty Images

In one of her most memorable fashion moments to date, Kerry Washington wore this gold sequin embellished two-piece Zuhair Murad dress featuring Egyptian motifs.

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Hunter Schafer (2020)

Hunter Schafer at the 2020 Vanity Fair Oscar Party — Karwai Tang / Getty Images

Hunter Schafer attended her first Vanity Fair Oscars Party in this playful Givenchy statement dress. The colorful dress came to life with rainbow fringe and plenty of sequins.

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Zendaya (2022)

Zendaya at the 2022 Vanity Fair Oscar Party — Axelle / Bauer-Griffin / FilmMagic

After walking the red carpet in a custom Valentino silky white cropped blouse and shimmering skirt, Zendaya changed gears and donned an androgynous double-breasted suit from Sportmax for the after party.

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Jessica Chastain (2022)

Jessica Chastain at the 2022 Vanity Fair Oscar Party — Lionel Hahn / Getty Images

Jessica Chastain celebrated her first Oscar win for Best Actress in The Eyes of Tammy Faye by changing out of one custom Gucci look into another. Chastain shined in a rose gold and lilac gown for the red carpet, but she took on a bolder look in a strapless emerald green number for the after party.

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Billie Eilish (2022)

Billie Eilish at the 2022 Vanity Fair Oscar Party — Lionel Hahn / Getty Images

Billie Eilish started closing in on EGOT status with her 2022 Oscar win, and she did so in style, of course. Billie walked the red carpet in a custom black tiered Gucci gown, but for the VF party, she changed into an archive Simone Rocha mini dress with over-the-knee combat boots.

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Serena Williams (2022)

Serena Williams at the 2022 Vanity Fair Oscar Party — Frazer Harrison / Getty Images

Serena Williams may be the GOAT when it comes to athletics but her red carpet game is just as strong. At the 2022 Academy Awards, Williams walked the carpet in a pink Gucci gown and embraced the after party spirit by changing into a glittering silver Versace mini dress.

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Ariana DeBose (2022)

Ariana DeBose at the 2022 Vanity Fair Oscar Party — Axelle / Bauer-Griffin / FilmMagic

Ariana DeBose "did the thing" in 2022 by taking home an Oscar for Best Supporting Actress while wearing Valentino Haute Couture. For the after party, she changed into a short black Monot look with a dramatic oversized bow.

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Tessa Thompson (2022)

Tessa Thompson at the 2022 Vanity Fair Oscar Party — Karwai Tang / Getty Images

Never shying away from a statement look, Tessa Thompson attended the 2022 Vanity Fair Oscars party wearing Schiaparelli Haute Couture. The outfit consisted of a structured black and white jacket, with matching bermuda shorts, black tights, and platform heels.

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Emily Ratajkowski (2022)

Emily Ratajkowski at the 2022 Vanity Fair Oscar Party — Daniele Venturelli / WireImage

In a love-it-or-hate-it fashion moment, Emily Ratajkowski wore this vintage Armani Privé bustier and skirt look to the 2022 party. The model kept her glam simple with a subtle smokey eye and straight hair to balance out the bold sequined outfit.

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