In a time of mass uncertainty, it can seem trite to look forward to award season. But after a year of quarantining at home, film and television have become a shared source of joy amid the perils of the pandemic. Sure, many of us have spent the last several months in nothing fancier than sweatpants, but how we dress has always been indicative of our collective psyche, and no other event quite represents the current state than a Hollywood red carpet. Since 1929, the Academy Awards has maintained firm footing in the zeitgeist not only by being a point of contention and conversation but also for history-making moments, including some of the best red carpet looks of all time. While some years are more memorable than others, we prefer to focus on the standout moments that made us smile. Sequins, satin, and sleeveless dresses may be timeless, but the best Oscars looks of all time aren’t always the safest bet—they’re daring, bold, and sometimes deemed "the worst” at first, but that’s what makes them iconic. Ahead, you’ll find the 49 Oscars looks that surprise and delight and that were truly indicative of the times.
WHO: Audrey Hepburn and Jean Hersholt
WHAT: 1954 Academy Awards
WEAR: On Audrey Hepburn: Givenchy gown
Oscars night 1954 was a major moment for Audrey Hepburn—not only did she win the Best Actress award for her breakout role in Roman Holiday, but it’s also worth noting that her custom-made Givenchy gown ushered in a new era in fashion. Hailed as one of the most classic dresses of the 20th century, this dress was indicative of Hepburn’s role as muse to French designer Hubert de Givenchy, and their relationship went on to change the way celebrities and designers worked together.
WHO: Grace Kelly and Edmond O'Brien
WHAT: 1955 Academy Awards
WEAR: On Grace Kelly: Edith Head gown and coat
It doesn’t get more glamorous than the future princess of Monaco, award-winning actress Grace Kelly. While she served quite a few iconic looks on- and off-screen, her custom-made Edith Head gown was her most iconic red carpet outfit for several reasons: That night, she took home the award for Best Actress (in the film The Country Girl), and it was one of the most expensive dresses worn to the ceremony, crafted from $4000 worth of French satin.
WHO: Elizabeth Taylor
WHAT: 1957 Academy Awards
WEAR: William Ruser tiara and earrings
Yes, gowns are an essential part of making the Oscars a true Hollywood affair, but let’s be honest: The jewelry really makes the night sparkle. No one quite knew the power of jewels like actress Elizabeth Taylor. After all, who else could pull off wearing a full-diamond tiara to the Academy Awards?
WHO: Barbra Streisand
WHAT: 1969 Academy Awards
WEAR: Arnold Scaasi pantsuit
Long before naked dresses and sheer jumpsuits were a thing, Barbra Streisand turned heads with her transparent pantsuit at the 1969 Academy Awards. Of course, the subtly sheer number was enhanced by the spotlights, but Streisand's star power—including taking home her first statue that night—was anything but accidental.
WHO: Cher and Sonny Bono
WHAT: 1973 Academy Awards
WEAR: On Cher: Bob Mackie two-piece gown
Any Cher fan knows that she’s spent the duration of her career serving up iconic looks (she pioneered the naked-dress trend), but none are seared into our brains quite like her 1973 Oscars look. This stunning sequinned two-piece Bob Mackie gown is the stuff of psychedelic ‘70s dreams—not to mention, she looks fantastic. Cher, please drop the core workout routine.
WHO: Farrah Fawcett and Marcello Mastroianni
WHAT: 1978 Academy Awards
WEAR: On Farrah Fawcett: Stephen Burrows gown
Farrah Fawcett’s slinky, gold Stephen Burrows gown rivals an Oscar statue itself.
WHO: Diana Ross and Ernest Thompson
WHAT: 1982 Academy Awards
WEAR: On Diana Ross: red sequin gown; white fur stole
If you’re coming out to the Oscars, you want to go all the way out. In the ‘80s, no one quite brought the glamour like singer and actress Diana Ross. This head-to-toe red sequinned gown is everything.
WHO: Whoopi Goldberg
WHAT: 1991 Academy Awards
WEAR: black sequin column dress; pearl necklace and earrings
There are very few artists in the world who have won an EGOT—Whoppi Goldberg is one of them. Goldberg is the first-ever African American to be nominated for Best Actress and Best Supporting Actress (which she won in ‘91 for her performance in Ghost). Her look for the 1991 Academy Awards encompassed the type of popular sequinned column dresses that were everywhere during the late ‘80s and early ‘90s, making it historic in and of itself.
WHO: Madonna and Michael Jackson
WHAT: 1991 Academy Awards
WEAR: On Madonna: Bob Mackie gown; Harry Winston diamond necklace and earrings
Sooner or later, when it comes to rounding up a list of iconic red carpet looks, you have to include Madonna. Her ‘91 Oscars outfit was one for the history books, as she channeled Marilyn Monroe with a sequinned sweetheart-neckline Bob Mackie gown and $20 million worth of Harry Winston jewelry. Material girls, this is your look.
WHO: Sarah Jessica Parker and Matthew Broderick
WHAT: 1993 Academy Awards
WEAR: On Sarah Jessica Parker: brown sequin gown; blue-lens sunglasses
Don’t get it twisted. Long before serving iconic on-screen looks as Carrie Bradshaw in Sex and the City, Sarah Jessica Parker was giving us head-to-toe ‘fits. Case in point: the simple yet very ‘90s brown sequin gown and blue-lens sunglasses she wore to the Academy Awards in 1993.
WHO: Vanessa L. Williams
WHAT: 1995 Academy Awards
WEAR: sequin and mesh gown; pashmina; clutch bag
Remember the chocolate-brown, sequin, and mesh number Vanessa L. Williams wore in ‘95? The gown—with its multiple fabrics, color, and cut—was far ahead of its time and includes almost every ‘90s trend we hold dear today.
WHO: Naomi Campbell
WHAT: 1996 Academy Awards
WEAR: yellow gown; diamond choker
Honestly, is it even a roundup of the best red carpet looks of all time without Naomi Campbell? What’s great about her 1996 Oscars look is the sheer understated elegance of it—the yellow floor-length gown with the halter cut paired with a diamond choker necklace is just too good for words.
WHO: Jada Pinkett Smith and Will Smith
WHAT: 1997 Academy Awards
WEAR: On Jada Pinkett Smith: two-piece Versace dress
Although this coordinated red carpet look from Jada Pinkett Smith and husband Will Smith may have been questionable at the time, it’s now a secret iconic gem. Not only was her vibrant green two-piece gown Versace, but the midriff-bearing look was also very indicative of the trends to come that would influence the future of all "risqué” red carpet looks.
WHO: Nicole Kidman and Tom Cruise
WHAT: 1997 Academy Awards
WEAR: On Nicole Kidman: Christian Dior Couture gown
When we think of the Oscars today, we think of couture, but that wasn’t the standard in 1997. Nicole Kidman’s stunning yellow Christian Dior Couture gown put newly appointed John Galliano on the map and couture on the carpet, elevating both the fashion industry’s profile in Hollywood and the Oscars red carpet for years to come.
WHO: Gwyneth Paltrow
WHAT: 1999 Academy Awards
WEAR: Ralph Lauren ball gown; Harry Winston diamond necklace and earrings
At the time of their debuts on the carpet, many of the most iconic Oscar looks were met with either fanfare or outright disgust. For Gwyneth Paltrow’s 1999 bubblegum-pink Ralph Lauren gown with $160,000 worth of Harry Winston diamonds, it was the latter. Why anyone wouldn’t love this look, we’re not sure, but does it matter? She took home the Best Actress award for her role in Shakespeare in Love and served one of the most remembered looks to date.
WHO: Celine Dion
WHAT: 1999 Academy Awards
WEAR: Dior suit; fedora; diamond-studded Ray-Bans
The fashion critics in ‘99 were particularly harsh on Oscars red carpet looks, including Celine Dion’s white Dior satin pantsuit by John Galliano, which she wore styled backward. Little did they know, this would become one of her most iconic looks ever and one of the most celebrated Academy Awards looks of all time. Guess it pays to think outside the box (or just to be Celine Dion).
WHO: Uma Thurman
WHAT: 1999 Academy Awards
WEAR: two-piece Chanel dress; bangle bicep cuffs
Something must have been in the water at the 1999 Academy Awards because it served us some serious looks, particularly this two-piece Chanel outfit from Uma Thurman. Of course, it wasn’t her first time stealing the red carpet (she championed a silk lavender Prada dress in ‘94), but it’s an outfit that has left many in their feelings.
WHO: Cameron Diaz
WHAT: 2000 Academy Awards
WEAR: Versace gown
While there are red carpet looks that are timeless, others, like a fine wine, take time to come into their own—that’s the case with Cameron Diaz’s ensemble for the 2000 Oscars. At the time, it could have been considered too risqué, but this see-through Versace gown, in many ways, was a precursor to the beloved naked dresses celebrities wear today.
WHO: Salma Hayek
WHAT: 2000 Academy Awards
WEAR: Eric Gaskins gown
Salma Hayek has donned some of the chicest Oscars red carpet looks over the years, but none are quite as lovely as her ‘00s ceremony gown. The lavender, beaded Eric Gaskins gown with a deep V-neck may not be the most exuberant dress ever worn on the red carpet, but its subtle elegance is what makes it worthy of being considered one of the best Oscars looks of all time.
WHO: Lucy Liu
WHAT: 2000 Academy Awards
WEAR: Versace dress
As editors, we’re always delighted when we come across a resurging trend or a forgotten incredible red carpet look—that is the case with Lucy Liu’s ‘00s Oscars ensemble. The stunning red and black, one-shoulder Versace gown needs to be brought back into the cultural psyche because it’s just too good.
WHO: Jennifer Aniston and Brad Pitt
WHAT: 2000 Academy Awards
WEAR: On Jennifer Aniston: Atelier Versace gown
The black dress is not a new concept to the red carpet, but no one can quite wear a deep V-neck black gown like Jennifer Aniston. Since her attendance at the ‘00s Academy Awards in Atelier Versace, she’s championed this cut time and again, but can you blame her? A dress this good deserves to be seen.
WHO: Halle Berry
WHAT: 2002 Academy Awards
WEAR: Elie Saab gown
There are numerous reasons why Halle Berry’s 2002 Oscars look can be considered one of the best of all time. Her half-sheer embroidered gown not only put Elie Saab on the map, but she also became the first Black woman to win Best Actress—talk about iconic.
WHO: Kate Hudson
WHAT: 2003 Academy Awards
WEAR: Atelier Versace gown
Encapsulating Hollywood glamour into a singular gown isn’t easy, but that’s precisely what Donatella Versace did with the stunning floor-length gold gown worn by Kate Hudson in ‘03. Every detail, from the hand-sewn embroidery to the 14k gold lining, on the effervescent Hudson makes this look worthy of its own award.
WHO: Charlize Theron
WHAT: 2004 Academy Awards
WEAR: Gucci gown
Charlize Theron’s performance in the film Monster isn’t the only thing worthy of an Oscar. Her red carpet look for the ‘04 ceremony is, too. Tom Ford designed the stunning strappy, bedazzled Gucci gown, and the pairing of Theron’s wavy hairdo and bleached eyebrows makes this a look we can’t forget.
WHO: Oprah Winfrey and Hilary Swank
WHAT: 2005 Academy Awards
WEAR: On Oprah Winfrey: Vera Wang gown; On Hilary Swank: Guy Laroche dress
What makes the Oscars red carpet unique is that the ensembles range from classic to cutting-edge at every ceremony. The two looks that distill the full scope of Oscar’s style are what Oprah Winfrey and Hilary Swank wore to the 2005 ceremony. Winfrey opted for a classic, fitted Vera Wang gown, while Swank donned a floor-length, open-back navy gown by Guy Laroche. The result? Two incredible women in two iconic looks that are worth thinking about.
WHO: Reese Witherspoon
WHAT: 2006 Academy Awards
WEAR: vintage Christian Dior gown
Reese Witherspoon’s ‘06 Oscars gown may be considered traditional by most, but what makes this Dior dress immaculate is that this champagne-colored beaded gown was found by her stylist in a vintage store in Paris. C'est magnifique.
WHO: Penelope Cruz
WHAT: 2007 Academy Awards
WEAR: Atelier Versace gown
I have yet to see an Atelier Versace red carpet look I did not love—Penelope Cruz’s ‘07 Oscar Awards ensemble is high up there for me. What’s fantastic about this look is that the pale-pink strapless gown has this stunning ruched bodice and full feather skirt, making it a dreamy, princess-like look that could only be embodied by Cruz herself.
WHO: Angelina Jolie
WHAT: 2009 Academy Awards
WEAR: Elie Saab gown; emerald earrings
My love for Angelina Jolie was cemented by her 2009 Oscars red carpet look. While some critics may consider the 2012 black high-slit Atelier Versace gown her best look of all time, I’ll go to bat for this look. Yes, the Elie Saab gown stole my heart, but Jolie’s stunning emerald earrings are what sealed the deal—the dramatic color contrast, the size, and her damn cheekbones just make this look too divine for humanity.
WHO: Zoe Saldana
WHAT: 2010 Academy Awards
WEAR: Givenchy Couture gown
Former cover star Zoe Saldana’s 2010 Oscars red carpet look is lauded as one of the best looks of all time (for a good reason). While the star was nominated for the film Avatar that year, it’s her dress that was the genuinely out-of-this-world thing—the sequins and ombré tulle make this Givenchy Couture gown designed by Riccardo Tisci a celestial piece of Oscars history.
WHO: Rooney Mara
WHAT: 2012 Academy Awards
WEAR: Givenchy Couture
While Rooney Mara’s red carpet style may appear to be simple from far away, the intricate details, textures, and fit say otherwise. Take, for example, her 2012 Oscars red carpet look. To the objective on-looker, she’s wearing a simple white gown, but for the fashion crowd, we know that this Givenchy couture was custom-made by Riccardo Tisci with pearl-colored lace.
WHO: Meryl Streep
WHAT: 2012 Academy Awards
WEAR: Lanvin gown and belt; Salvatore Ferragamo shoes
Meryl Streep stirred up the whole pot at the 2012 Academy Awards—not just because she won Best Actress for her performance as Margaret Thatcher in The Iron Lady. Her choice of Lanvin garnered considerable discussion among the industry not just because people were unsure about the full-gold look but also because Streep selected Lanvin over Chanel for the ceremony. No matter what the tea is, this look is one we’ll be talking about for years to come.
WHO: Jennifer Lawerence and Anne Hathaway
WHAT: 2013 Academy Awards
WEAR: On Jennifer Lawerence: Dior Haute Couture gown; On Anne Hathaway: Prada gown
If you were to take a time machine back to the 2013 Oscars, you’d know that the buzz was all about Jennifer Lawerence and Anne Hathaway. Lawrence’s fall up the stairs to her acceptance speech and Hathaway’s "controversial” dress were the talk of the town. But the attention should have been focused on how they both handled the night with such grace (which is easy to do when you’re wearing Dior or Prada) and took away Oscars, too.
WHO: Lupita Nyong'o
WHAT: 2014 Academy Awards
WEAR: Prada gown; Fred Leighton jewels and headband
Genuinely speaking, there is not a more iconic Oscars red carpet moment in recent history than Lupita Nyong’o’s 2014 ensemble. What made this look historic (other than her win of Best Supporting Actress that year) was this crystal-pleated, powder-blue, deep V-neck Prada gown. We could stare at this look forever.
WHO: Jennifer Lopez
WHAT: 2015 Vanity Fair Oscar Party
WEAR: Zuhair Murad Couture dress; white fur.
It’s no secret that Jennifer Lopez has her fair share of iconic looks; however, none quite hold the same place in my heart as her 2015 Oscars After-Party outfit. Yes, her Ellie Saab gown for the ceremony was stunning, but nothing quite distills the "J.LO aesthetic” like this full-length sequin Zuhair Murad Couture dress and white fur stole. My only question is, does love not cost a thing? Because this gown sure looks like a million bucks.
WHO: Emma Stone
WHAT: 2015 Academy Awards
WEAR: Elie Saab gown
Let it be stated for the internet records that Emma Stone is secretly that girl who always brings her A game to the red carpet. Case in point: the green floor-length, high-slit, and sequinned Elie Saab gown she wore to the 2015 Academy Awards. This isn’t a bad look; it’s a super-bad look if you catch my drift.
WHO: Jane Fonda
WHAT: 2015 Vanity Fair Oscars Party
WEAR: Zuhair Murad Haute Couture jumpsuit
Whenever I see another red carpet look from the one-and-only Jane Fonda, I always pray that I can look as fabulous as her when I grow up. Of course, it doesn’t hurt to be able to wear a full-sequin Zuhair Murad Haute Couture jumpsuit, but then again, it’s Jane Fonda, and no one else can serve a red carpet look like her.
WHO: Kerry Washington
WHAT: 2016 Academy Awards
WEAR: Atelier Versace gown; Schutz shoes
Whether you’re a Scandal fan or just a Kerry Washington stan, the power of the ensemble she wore to the 2016 Oscars can not be understated. She slayed that carpet like a gladiator in head-to-toe (the ponytail, the Atelier Versace gown with a leather bodice and a high-slit, and the see-through Schutz heels) perfection.
WHO: Zendaya
WHAT: 2018 Academy Awards
WEAR: Giambattista Valli Couture dress; Brian Atwood shoes; Bvlgari jewelry
There’s not a day that goes by that I don’t think about the incredible celebrity and stylist pairing that is Zendaya and Law Roach. The style companions have served us some of the most iconic red carpet looks to date, including this stunning floor-length, off-the-shoulder, chocolate-brown Giambattista Valli number. Zendaya, why do you do this to me?
WHO: Saoirse Ronan
WHAT: 2018 Academy Awards
WEAR: Calvin Klein dress; Christian Louboutin shoes; Cartier jewelry
Compared to the over-the-top numbers the Oscars red carpet has seen in the past, Saoirse Ronan’s strapless pink Calvin Klein dress isn’t overly exuberant. But the oversize bow in the back makes this a lesson in understated elegance. This look could have been worn to the Oscars in the ‘50s or could easily make a statement well into the future. That’s what makes it iconic.
WHO: SZA
WHAT: 2019 Academy Awards
WEAR: custom Vivienne Westwood dress; Jennifer Behr hairpins; Bvlgari jewelry; Stuart Weitzman Nudist Disco shoes
The great thing about the Oscars is that sometimes our favorite musicians will be nominated for film scores and show up wearing some of the best looks of the night—that was the case with SZA’s 2019 Oscars look. The stunning custom Vivienne Westwood dress with a corset bodice and a frayed hem had her looking like a supermodel.
WHO: Billy Porter
WHAT: 2019 Vanity Fair Oscars Party
WEAR: Christian Siriano tuxedo dress
The Oscars red carpet hasn’t always been known to host the boldest looks from nominated actors and attendees, but every once in a while, we’re blessed with a few men who aren’t afraid to go bold. It doesn’t get bolder than actor and style icon Billy Porter—who else could pull off a Christian Siriano tuxedo dress? Like it or not, this is an Oscars red carpet look we’ll be talking about for years to come.
WHO: Gemma Chan
WHAT: 2019 Academy Awards
WEAR: Valentino Haute Couture dress; Bvlgari jewelry; Jimmy Choo shoes
No one has ever entirely made a case for hot pink on the Oscars red carpet like Gemma Chan. Her voluminous Valentino Haute Couture gown is something I stare at when I feel I need a reminder that there are, indeed, beautiful things in the world.
WHO: Regina King
WHAT: 2019 Academy Awards
WEAR: Oscar de la Renta dress; Chopard jewelry; Christian Louboutin shoes
The 2019 Academy Awards was a huge night for Regina King, as she not only won Best Supporting Actress for the film If Beale Street Could Talk, but she also donned one of her best red carpet looks to date. Of course, King fans are well aware that she’s often one of the most stylish characters on-screen, but the stunning white Oscar de la Renta gown paired with matching Christian Louboutin shoes proved she’s a style icon IRL, too.
WHO: Lady Gaga
WHAT: 2019 Academy Awards
WEAR: Alexander McQueen dress; Tiffany & Co. jewelry
If you weren’t already a self-proclaimed Little Monster (like myself), the 2019 Oscars could have felt as if a star was born that evening. Of course, real Lady Gaga fans know she’s served iconic looks for years; her Oscar win (for best original song), the Alexander McQueen dress, and the yellow Tiffany & Co. necklace had her shinin’ like never before.
WHO: Janelle Monáe
WHAT: 2020 Academy Awards
WEAR: Ralph Lauren custom evening dress; Forevermark jewelry
I’ve said it before, and I’ll repeat it: Janelle Monáe does not play when it comes to her style. No gown better encompasses that ethos than the crystal-lacquered silk lamé, tulle mesh Ralph Lauren gown—featuring a draped hood and an open back—she wore to the 2020 Oscars. It took over 600 hours of handwork to embroider 168,000 Swarovski crystals on the dress, making it a masterpiece we won’t forget.
WHO: Timothée Chalamet and Margot Robbie
WHAT: 2020 Academy Awards
WEAR: On Timothée Chalamet: Prada jacket and trousers; Cartier Tradition brooch
If you know, you know that Timothée Chalamet is never one to shy away from serving a look. (He’ll wear men’s jewelry with ease.) Of course, that fearlessness is sometimes met with mass critique, most recently including strong feelings around his 2020 Oscars outfit. Instead of sticking to a tuxedo, he opted for an anti-suit: a Prada Re-Nylon gabardine jacket with satin racing stripes and matching Prada Re-Nylon trousers over a white poplin shirt. He finished the look with a Cartier Tradition brooch with 18k white gold, platinum, rubies, and diamonds. While the critics may not have been here for it, I have a feeling this look will go down in history as ushering in a new way for men to approach their Oscars red carpet looks.
WHO: Sandra Oh
WHAT: 2020 Vanity Fair Oscars Party
WEAR: Cong Tri dress; Messika jewelry; Stuart Weitzman shoes
One person can bring life or death by serving a look, and that’s no other than Grey’s Anatomy and Killing Eve star Sandra Oh. Her 2020 Vanity Fair Oscars Party look (a gray, floor-length, sequinned, feather-embellished, deep V-neck Cong Tri dress) had me in shambles.
WHO: Janet Mock
WHAT: 2020 Vanity Fair Oscars Party
WEAR: Oscar de la Renta dress
By now, you know that a list of the best Oscars looks of all time is subjective and ever-changing in the face of trends. Occasionally, there are hidden gems—like this Oscar de la Renta look Janet Mock wore to the Vanity Fair Oscars Party—that go unnoticed. But with time, reflection, and a whole lot of sequins, we’re able to see that the best Oscars looks of all time strike the perfect balance between being timeless and being of that time period. How to know if something can be considered stylish is in the eye of the beholder, I guess, but for now, I’ll keep staring at these looks.
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