Sequins, Capes, Beading and a Bow: Revisiting the Best Oscars Looks of All Time

From Hilary Swank's backless dress to Lupita Nyong'o's pearl gown, these are the Oscars looks that continue to be the best of the best. Take a glamorous walk down memory lane with E! News.

By Samantha Schnurr Apr 26, 2021 4:00 PMTags
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If there's anything that can steal the spotlight from an Academy Award—it's a stunning Oscars outfit

As anyone who looks forward to Hollywood's biggest night well knows, there have been plenty of standout ensembles in the course of the award ceremony's nine-decade history. As the event where dressing to impress is more of an expectation than an option, the Oscars red carpet has become the place to unveil breathtaking fashion. Whether an exquisite ballgown or an inventive jumpsuit, the boundaries for what makes a stellar Oscars look continue to expand—but style is always at its core. 

So, in the nearly 100 years that Hollywood's brightest stars have gotten dressed up for the special night, which looks continue to stick out as the crème de la crème? Lupita Nyong'o's custom Calvin Klein gown from 2015, for one? The showstopping creation featured more than 6,000 pearls, one of the reasons it remains unforgettable to this day. 

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There's the Brandon Maxwell jumpsuit-ballgown hybrid Lady Gaga donned in 2016 or the Alexander McQueen sculptural gown—with matching gloves and an estimated $30 million Tiffany diamond necklace—she wore on the red carpet in 2019 before winning her first Oscar. 

Of course, that's just skimming the surface of the Oscars' ultra glamorous sartorial history. With the 2021 ceremony officially in the history books, a few more one-of-a-kind looks have been added to the annals of Oscar fashion. Revisit the best Oscars ensembles of all time below. 

Lupita Nyong'o

The Oscar winner was the definition of glamour in this pearl gown by Calvin Klein in 2015. 

Kate Hudson

Of her many appearances at the Academy Awards, Kate Hudson's look for the 2014 Oscars stands out as one of the very best, thanks in part to this caped and beaded Atelier Versace gown. 

Chrissy Teigen

While accompanying her Oscar-nominated husband John Legend in 2015, Chrissy Teigen was the epitome of modern Hollywood glamour in this periwinkle Zuhair Murad gown. 

Lady Gaga

For the ceremony where she ultimately won her first Oscar, Mother Monster arrived dressed to take everyone's breath away in an Alexander McQueen structural gown paired with an estimated $30 million Tiffany's necklace

Halle Berry

The actress' Oscar win was unforgettable for many reasons. She was the first black woman to win the Best Actress award, which she won in 2002 for Monster's Ball. Aside from her historical win, her Oscar-winning dress instantly became iconic and it arguably put designer Elie Saab, on the map.

Lupita Nyong'o

The Black Panther actress always knocks it out of the park during awards season, or any season, for that matter. She wore this baby blue, custom-made Prada gown at the 86th Annual Academy Awards. This marked the first time she won the Best Supporting Actress award for her debut film 12 Years a Slave.

Gwyneth Paltrow

The drool-worthy cape dress that shut down the red carpet for its elegant yet edgy design. It's safe to say Tom Ford outdid himself with this number on the actress.

Kacey Musgraves

The country singer knows how to turn heads and this bubblegum pink Giambattista Valli number was proof. From its massive ruffled hems to the billowing tulle sleeves and flashy jewel-encrusted brooch, this lewk was everything.

Lady Gaga

The A Star is Born actress looked effortlessly elegant in a white pantsuit-dress by Brandon Maxwell. She was a vision in white, and exuded old Hollywood glamour with her coiffed hair and fresh-faced makeup.

Viola Davis

The Oscar-winning actress stunned in this electrifying hot pink gown by Michael Kors. In addition to her bright and bold dress, she accessorized with a matching flamingo pink clutch and statement jewelry pieces.

Ava Gardner

The silver screen siren of the Golden Age of Hollywood dazzled in an ostentatious sequins gown. As if that weren't glamorous enough, she wore a large and lustrous tiara, white fur and gloves.

Gemma Chan

Perfectly pink! The Crazy Rich Asians star makes a grand entrance with her bright and bold Valentino design. Plus, the added pockets are a chef's kiss.

Janelle Monáe

Never one to stick to the basics, the Moonlight actress made the 2017 Oscars red carpet her runway. She wore a jaw-dropping Elie Saab Haute Couture gown, which was adorned with intricate beading, lace set with feathers and an over-the-top tulle train.

 

Yalitza Aparicio

The Roma actress brought a fashion fantasy to the red carpet with her dreamy and whimsical Rodarte design.

Regina King

The Watchmen actress knows how to make a statement with a simple but sophisticated lewk.

Hilary Swank

The 44-year-old star took home the Best Actress award for Million Dollar Baby and the award for best-dressed. Her Guy Laroche design was simple, yet striking as the silk gown featured a plunging open-back. 

Diana Ross

Diana Ross sizzled at the 54th Annual Academy Awards in a glittering red gown and lush white fur shawl.

Billy Porter

Strike a pose! The actor and fashion icon proved why he reigns supreme on the red carpet, and this tuxedo dress is proof! He wore Christian Siriano.

Nicole Kidman

The Big Little Lies actress always shuts down the red carpet, and this powerful red gown by Balenciaga was no different. The high-neck, sleeveless design made it simple and classic, but the dramatic bow and striking color, took it to the next level.

Tessa Thompson

The actress took a fashion risk at the 2019 Oscars... and it most certainly paid off!

Elizabeth Taylor

One word: Glamourous. The legendary actress knew how to work a dress, and this elegant design was no different.

Zoe Saldana

Wearing a custom Atelier Versace design, the Guardians of the Galaxy actress stunned in her blush-colored, body-hugging gown.

Jennifer Lopez

It's always fun to see what daring design the 49-year-old star will wear on the red carpet. At the 2015 awards show, she kept things classic, but not boring. She wore an elegant Elie Saab dress, which featured ornate beading and a full, chiffon tulle train.

Debbie Allen

Serving us serious glamour, Debbie Allen wowed the crowd with her performance at the 54th Annual Awards. In addition to her on-stage performance with Gregory Hines, she stunned in an eye-catching lavender gown, which featured white-beaded fringe and a thigh-high slit.

Margot Robbie

The Aussie actress exuded old Hollywood glamour in her full-length, long-sleeve Tom Ford gown.

Penélope Cruz

The Everybody Knows star shined as bright as the flashing lights with her blush-colored Atelier Versace gown. The design featured a chiffon bodice with an organza tulle train.

Gina Rodriguez

The Jane the Virgin star brought the glitz and the glam to the 2018 awards show. Rodriguez hit the red carpet in a nude-colored Zuhair Murad gown, which was emblazoned with ornate beads and a billowing chiffon train.

Salma Hayek

The Frida star stunned on the Oscars red carpet in one of the hardest colors to pull off. She wore an eye-catching ocean blue Atelier Versace gown to the star-studded event.

Meryl Streep

The legendary star holds the record for having the most Academy Award nominations of any actor, and her 2012 ensemble was just as noteworthy as her accomplishments. She dazzled in a gold lamé gown designed by Lanvin.

Reese Witherspoon

The Big Little Lies actress always dresses like a Southern belle, but at the 2006 awards show, she also brought her Southern charm. The star looked statuesque in her 1955 Christian Dior gown, which she found at a Paris vintage boutique. Rumor has it, the boutique owner had a tough time parting ways with it, because it allegedly once belonged to royalty.

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