25 of The Best Oscars Red Carpet Looks of All Time

Iconic outfits only.

best oscars fashion

Halle Berry / Gemma Chan / Zendaya

Some people watch the Super Bowl for the athletes. There are certain groups of people that attend the U.S. Open for the love of tennis. But then there are fashion people. The Oscars? Sure, it's wonderful to celebrate milestones in cinematic history, but we're here for the red carpet. It's about the glamour, the off-the-shoulder drama and the gossip, and last minute fashion tape of it all.

These are one writer's favorite looks based zero percent on the film being represented or the context of the given awards show. True icons are timeless, and so are these looks. They speak to a deeper cultural movement, a moment in time, or in some cases, they're just really fantastic ensembles. Read on for 25 of our favorite fashion moments worthy of their very own Oscar.

Nicole Kidman in Dior (1997)

nicole kidman

Kevin Mazur Archive / WireImage

Sometimes more is more is more. This is certainly the case with Nicole Kidman's Christian Dior look for the 69th Academy Awards. Tom Cruise is a but a shadow in the glory of this impossible-to-name lime and glorious mess of textures.

Gwyneth Paltrow in Ralph Lauren (1999)

Gwyneth Paltrow

Frank Trapper / Corbis via Getty Images

The folklore that surrounds this dress is worth an Oscar of its own. There's something innocent and delightful about the dress, whether or not its fit is a little off. GP looks thrilled to be there, and no best dressed list is complete without this outfit.

Lupita Nyong'o in Prada (2014)

lupita nyong'o

Christopher Polk / Getty Images

Lupita's iconic Prada dress from 2014 singlehandedly elevated the Grecian goddess trope. Just when we thought teal was over for good, this dress graced the red carpet. Accessorized with a pearl headband and a shining golden man, this look is still a winner.

Grace Kelly in Edith Head (1955)

grace kelly

Silver Screen Collection / Hulton Archive/Getty Images

Thin straps and white gloves, this look from the '50s is remarkably on-trend for 2022. Grace Kelly wore a matching duster in the same shade of perfect aqua. A simple updo completed the look, epitomizing timeless glamour.

Faye Dunaway in Theadora Van Runkle (1968)

faye dunaway

Bettmann / Contributor / Getty Images

This look predates stylists, which makes it all the more fabulous. A black feather-lined duster with tights and black shoes feels impossible to place in one specific era. It's unexpected and cool—a combination that's rare to come across at the Academy Awards.

Lauren Hutton in Halston (1975)

lauren hutton

Michael Montfort / Michael Ochs Archives / Getty Images

Hutton's rainbow-colored Halston creation has found its way onto the mood boards of countless designers. And why wouldn't it? Worn with the neutral fur jacket, it's the best of '70s glamour bottled into a single outfit, made all the better by Lauren Hutton's undeniable charm.

Winona Rider in Armani (2000)

winona ryder

 Ke.Mazur / WireImage

Often re-worn, this Armani dress has been a long-standing favorite of the actress. It's textbook LBD with her exacting sense of nonchalance. The headband and sash elevate the look without distracting from the striking silhouette.

Whitney Houston (1994)

whitney houston

Steve Starr / CORBIS / Corbis via Getty Images

Leave it to Whitney Houston, a performer at the 66th Academy Awards, to school the entire red carpet on the power of a suit. The look was cemented as a greatest of all time with a choker necklace and bra detailing peeking out from wide lapels.

Sharon Stone in Vera Wang and Gap (1998)

sharon stone

KMazur / WireImage

Another master class, and this time in the art of high/low dressing. Sharon Stone wears a plain, white button-up from Gap with a lilac, floor-length skirt by Vera Wang. Her short hair and bold lips prove this outfit's the secret to laidback cool for a formal event.

Halle Berry in Elie Saab (2002)

halle berry

Jeff Kravitz / FilmMagic

Before there was the naked dress, there was Halle Berry at the 2002 Oscars. This look from Elie Saab feels sexy and ethereal through colorful details that give the dress a personality of its own. Her Oscar win was a watershed moment, as was this unforgettable work of art.

Hilary Swank in Guy Laroche (2005)

hilary swank

Jeff Kravitz / FilmMagic

In another case of "before it was a trend," Hilary Swank wore a down-to-there backless dress in a sophisticated navy blue in 2005. Understated, especially in the front, the dress remains an example of the power of doing less.

Diane Kruger in Elie Saab (2006)

diane kruger

Chris Polk / FilmMagic

This look single-handedly changes my mind about strapless dresses every time I see it. Kruger looks smashing in a structural creation by Elie Saab. Her undone hair gives the whole look a Californian ease.

Keira Knightley in Valentino (2015)

keira knightley

Jeffrey Mayer / WireImage

Here, Keira Knightley ushers in an era of fairytale dresses from Valentino. This dress is a refreshing departure from tight, jewel-tone numbers. Plus, it plays heavenly with her baby bump.

Margot Robbie in Chanel (2018)

margot robbie

Kevin Mazur / WireImage

There's something architectural about Margot Robbie's Chanel look from 2018. Her blunt bob gives the whole outfit a casual nature. Her crystal handbag evokes Old Hollywood for a winning combination of old and new.

Janelle Monáe in Ralph Lauren (2020)

Janelle Monáe

Steve Granitz / WireImage

Janelle Monáe is one of few people who could pull of a silver hood on the red carpet in a way that feels easy and instinctual. This outfit, designed by Ralph Lauren, is truly the first of its kind, in an homage to its wearer.

Cher in Bob Mackie (1973)


Michael Ochs Archives / Getty Images

There's so much to love about this look from Cher. The two-piece set seems commonplace now, but it hasn't always been the norm on the red carpet. Cher's stick straight hair gave even her most daring of outfits a sleek, '70s chill to them.

Taraji P. Henson in Reem Acra (2017)

taraji p henson

 Kevork Djansezian / Getty Images

The look is giving Angelina Jolie, but in a way only Taraji P. Henson can. Black velvet with a slit sounds like a safe bet, but with jewels like that, Henson proves she can create a look that's anything but boring.

Gemma Chan in Valentino (2019)

gemma chan

Dan MacMedan / Getty Images

Imagine this look as the most elevated version of "This dress has pockets!" Gemma Chan checks all the boxes for a high-glamour look, while still remaining her incredibly posh self.

Zendaya in Giambattista Valli (2018)


Kevin Mazur / WireImage

Here Zendaya is pictured in the picture-perfect look for any presenter to wear to the Oscars. Take notes! She's both stylish and laid-back, without a sequin in sight.

Tessa Thompson in Chanel (2019)

tessa thompson

Frazer Harrison / Getty Images

As an ode to Karl Lagerfeld, Tessa Thompson shone in this Chanel dress in 2019. Her half-back hair style, and the kitsch of the peplum waist give the look a retro glam feel.

Julia Roberts in Valentino (2001)

julia roberts

Mirek Towski / FilmMagic

Sure, it's not the most electric pick of all time, but this Julia Roberts look finds its way into almost every "best dressed" conversation. The simplicity of the dress really is remarkable. That winning smile and those stripes are special all on their own.

Martha Plimpton in Vintage (1989)

martha plimpton

Barry King/WireImage

This look belongs in my personal hall of fame for greatest looks of all time. River Phoenix and Martha Plimpton couldn't be cooler in their vintage looks. Timeless doesn't even begin to cover the way they could be dropped into any decade with these flawless outfits.

Diahann Carroll (1969)

Diahann Carroll

Michael Montfort / Michael Ochs Archives / Getty Images

There's something angelic about this beautiful, full-sleeved dress Diahann Carroll wore to present at the Oscars in 1969. The tiny floral detailing takes the look to another level. Very '60s eyelashes and colorful eye shadow complete the look.

Claire Danes in Versace (1997)

claire danes

Kevin Mazur Archive / WireImage

Skirt and shirt outfits are few and far between at the Academy Awards. Claire Danes feels like a cool older cousin in this teal set from 1997. Both underdressed, and somehow, buttoned up, this look is an example of one that works way better than it seems like it would on paper.

Barbra Streisand in Arnold Scaasi (1969)

Barbra Streisand

Bettmann / Contributor

This groundbreaking look from Miss Streisand often gets overlooked in the conversation of best Oscar outfits. It's the epitome of a classic, era-defining outfit. The oversized collar, the wide legs, the sheer detailing. It's a perfect look.

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