Halle Berry in Elie Saab, 2002

"This was the year Halle Berry became the first Black woman to win a Best Actress Oscar (for her performance in Monster's Ball). An iconic, history-making moment requires an equally iconic gown, and Saab delivered with this one. The blood-red lower half combined with the sheer floral top made for a sexy and sultry gown that is seared into my brain." — Nikki Ogunnaike, Senior Digital Director

Cher in Bob Mackie, 1986

"Cher’s look by Bob Mackie in 1986 made a splash for so many reasons. She had hoped for a nomination for Mask, but she was snubbed. Instead of staying home, she took the narrative in her own hands and appeared wearing this show-stopping set. I love that she fearlessly owned this unforgettable moment." — Jaclyn Cohen, Senior Fashion and Accessories Editor

Nicole Kidman in John Galliano for Christian Dior, 1997

"In 1997 it was nearly impossible to upstage Tom Cruise, but Nicole Kidman managed to draw attention away from her wildly famous husband on the Oscars red carpet with this silk dress by John Galliano, who had recently been appointed creative director of Dior. The way she pulls off the color is, of course, what made it so memorable—most people don’t look this smoking hot in chartreuse. Studying it now, though, I’m struck by the fantastical details, like the embroidered flowers and the mink lining. The shape is very ‘90s, but the embellishments feel like they’re from a fairy tale. Kidman was a star before this dress, but it confirmed her role as a major Hollywood player."—Izzy Grinspan, Deputy Editor

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Björk in Marjan Pejoski, 2001

"It's funny to me that people wrote off Björk's swan dress as silly when it first walked down the Oscars red carpet in 2001, because it is now considered one of the most iconic dresses of all time. Even people who don't love fashion or red carpets or Björk know about the swan dress. It's one of those fashion references that can unite us all, and I know this as fact because every time I tell someone my dog is named Björk, they ask if she owns a swan dress (she does).

To me, the swan dress just proves how powerful fashion can be. Björk clearly wore it as an act of rebellion; she was never trying to blend into the sea of Armani gowns. It's refreshing to see someone so sure of their personal style and sense of self that they feel comfortable wearing something so bold on one of the biggest fashion stages. And the dress itself was based on a swan costume worn by Marlene Dietrich—what's more elegant and lavish than that?!"—Tara Gonzalez, Senior Fashion Editor

Chloe Zhau in Hermès, 2021

"Chloe Zhao won the Oscar for best director for Nomadland in 2021, making her the first woman of color to take home the award. She accepted the Oscar in a look that I can only inadequately describe as extremely cool: a muted, putty-colored Hermes dress (that was intricately pleated and beaded if you zoomed in) and simple white sneakers. A total subversion of red carpet expectations. Brilliant."—Leah Chernikoff, Executive Editor

Gwyneth Paltrow in Tom Ford, 2012

"Gwyneth Paltrow at the 2012 Oscar exuded elegance in a white Tom Ford cape gown. I remember seeing her in this look and thinking 'Wow, she looks so royal.' From her hairdo to the carefully curated jewelry pieces, she had such a sophisticated presence on the red-carpet."—Alicia Banilivy, Fashion and Retail Credits Editor

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Salma Hayek in Armani, 1997

"Salma Hayek at the Oscars in 1997 is how a modern-day princess should dress. I love how she is wearing a full tiara in her hair, but the simplicity of the dress and heels makes the look feel low-key in an extremely fabulous way. The after-party photos of her in this Armani are even better; she's dancing with Fran Drescher and playing thumb wars on a beer-soaked table. She looked so polished but she wasn't acting precious, and to me that's the epitome of chic." —Tara Gonzalez, Senior Fashion Editor

Lauren Hutton in Halston, 1975

"Lauren Hutton at the 1975 Oscars is a singular look. She was wearing a sherbet-striped plunge-neck dress by Halston, a designer of the moment. The ease with which Hutton wears it is a testament to Halston's intuitive style of design. But the piece de resistance is the red fox fur jacket that Hutton threw on top on her way in. It doesn't seem like it should work: auburn and pastels? But the strangeness of it makes it look even more naturalistic. She really looks like she styled herself, with no interlocutor helping her look so picture perfect. Instead, Hutton looks like she's expressing her distinctly personal definition of glamour."—Rachel Tashjian, Fashion News Director

Zendaya in Valentino, 2022

"Zendaya dominated the Red Carpet at the 2022 Oscars. Her two-piece look featured a jaw-dropping Valentino Haute Couture white cropped shirt and silver sequin-embroidered evening skirt, styled with stacks and stacks of Bulgari Serpenti Viper bangles in white-gold all-pave. Maxi skirts are so in right now and to take that concept into formalwear with a crop shirt was so unexpected in the most brilliant way. She’s young and a force to be reckoned with in the fashion world. I loved this look so much." —Alicia Banilivy, Fashion and Retail Credits Editor

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Rihanna in Alaïa, 2023

"I really loved Rihanna’s baby bump moment at the 2023 Oscars just after she revealed that she was pregnant at the Super Bowl. Her custom Alaia dress was perfect, especially in the subtle details like the side slits and sheer fabric over her belly." —Brooke Bobb, Fashion News Director

Claire Danes in Narcisco Rodriguez, 1997

"Claire Danes at the 1997 Oscars is the chicest at 17. This Narcisco Rodriguez look is as cool then as it would be now. Love the color, love that it's a two-piece, love the child-like blue flower reef necklace and earrings with a the-Row-esque handkerchief satin bag and thinly strapped crystal sandals."—Miguel Enamorado, Accessories Director

Diahann Carroll in, 1969

"No one has ever looked more regal at the Oscars than Diahann Caroll in this embellished gown. The sleeves here are the star, hanging off her arms like clouds speckled with stardust. It's funny because she was presenting the award for best special effects that year, but I'm honestly having a hard time believing anything could be as mesmerizing as her gown." —Tara Gonzalez, Senior Fashion Editor

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Chloë Sevigny in Yves Saint Laurent, 2000

"Ahead of her Oscar nomination for Boys Don't Cry, Sevigny exclusively wore Alber Elbaz for Yves Saint Laurent. And whenever I think of the perfect black dress, I think of this one. The fabric flows like liquid, and so does Sevigny's confidence. She didn't walk in this, she floated. The deep V is sexy, too, but the most sultry aspect to me is the silver Maltese cross, made better by the mixed metal styling of her stack of gold bangles. I also adore the red nails and matching red lip, which further takes this look into a goth-esque territory the Oscars red carpet isn't particularly known for. The look is also just so her, and it makes me so happy to see someone expressing themselves in a way that feels both glamorous and genuine."—Tara Gonzalez, Senior Fashion Editor

Sharon Stone in Vera Wang, 1998

"Sharon Stone didn't wear a dress to the 1998 Academy Awards, but she wore a look. A borrowed Gap button-down and a silky Vera Wang skirt were maybe the last combination anyone expected on Hollywood's flashiest red carpet. Yet with the buttons almost all the way undone and the collar slightly popped, she made '90s styling history that lives on in designers' and stylists mood boards today. (Just see the 2022 Oscars red carpet, where Zendaya's white shirt and sequin skirt combination read like a glamorous homage.)" — Halie LeSavage, Fashion Commerce Editor

Gemma Chan in Valentino, 2019

"This Gemma Chan look is the definition of opulence to me because it has pockets!!! Nothing is more luxurious then a woman who appears to be lounging while on the red carpet. The color is also unbelievably striking — it's as though Pierpaolo Piccioli made it with her specifically in mind." —Tara Gonzalez, Senior Fashion Editor

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Gwyneth Paltrow in Ralph Lauren, 1999

"Gwyneth Paltrow’s Ralph Lauren gown in 1999 might just be the reason people say 'pretty in pink.' It was understated elegance, yet made an everlasting imprint on pop culture and American fashion. That was also the night she became an Oscar winner, taking home Best Actress for Shakespeare in Love!" —Jaclyn Cohen, Senior Fashion and Accessories Editor

Lupita Nyong'o in Prada, 2014

"my pick is Lupita's custom sky-blue Prada gown from 2014, when she was nominated for 12 Years a Slave. The dress literally has its own wiki page. I just remember so clearly when she walked down the carpet and the night felt like it belonged to her, this was truly her coming out party"— Faith Brown, Senior Social Media Manager

Winona Ryder in Chanel, 1997

"There's something about a black dress worn with a red lip on the Oscars red carpet that gets me. It's just so devastatingly cool, and no one does that better than Winona Ryder. This beaded, '20s-inspired Chanel dress from the 1997 Oscars is both dainty and vampy. I could spend all day talking about the embellishments, the framing neckline, the scalloped sleeves that expose her shoulders just so, her pointy black heels peeking out from the lace at the bottom...I love it all so much."—Tara Gonzalez, Senior Fashion Editor

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Jennifer Lopez in Valentino, 2003

"The vintage Valentino gown Jennifer Lopez wore to the 2003 Oscars was so old Hollywood with a modern twist. Perfectly — and, for her, minimally — accessorized, the dress made her shine in that beautiful shade of green. She looked like a movie star, and on her arms: her leading man, now her husband! So classic and so chic."—Miguel Enamorado, Accessories Director

Barbra Streisand in Arnold Scaasi, 1969

"To the first-ever televised Academy Awards in 1969, Barbra Streisand wore this unforgettable sequined pajama pantsuit by Arnold Scaasi. The collar, the bow, the cuffs, the absolute sheerness of it all — it's still a little shocking and so totally modern. Streisand won that year for Funny Girl, tying with Katherine Hepburn. (That's the first and only time that's happened too!)" —Leah Chernikoff, Executive Editor

Tara Gonzalez is the Senior Fashion Editor at Harper’s Bazaar. Previously, she was the style writer at InStyle, founding commerce editor at Glamour, and fashion editor at Coveteur.

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