The Oscars are one of the most-watched red carpet events in the world (along with the Met Gala, of course) and the 97th annual Academy Awards on March 15 will surely deliver plenty of memorable fashion moments. Hollywood’s brightest stars are expected to hit the red carpet in their most dramatic looks, since stylists often keep their best gowns and suits for last. In honor of the event, Vogue is looking back at some of the best Oscar dresses of all time.
Selected by our editors (past and present), this definitive list of top Oscar fashion moments revisits many iconic looks. Just last year, highlights included The Substance’s Demi Moore in sculptural, statuette, and silvery Giorgio Armani Privé, and Ariana Grande in pale-pale-pink and floaty Schiaparelli number—the Golden Age of Hollywood was a real theme across awards season.
Looking back over Oscars gone by? A crowd favorite was Rihanna in her baby bump-bearing Alaïa number in 2023, complete with leather accents, as well as Lupita Nyong’o’s sky-blue Prada gown from 2014, when the actress took home Best Actress for 12 Years a Slave. Nicole Kidman’s unexpected Balenciaga halter dress with a dramatic bow detail, which she wore in 2007, was another hit. And who could forget Charlize Theron’s glittering Gucci gown from 2004, when she accepted an Oscar for Monster looking the part of a true Hollywood star?
Many picks are some of the Oscars’s more unexpected style moments, too: Céline Dion’s backwards Christian Dior tuxedo, Björk’s Marjan Pejoski swan dress, and Cameron Diaz’s slightly boho dress by Emanuel Ungaro Couture, among others. As for throwback hits, Barbra Streisand’s sheer jumpsuit by Arnold Scaasi, worn in 1969, is proof that having fun on the carpet always wins, as does Salma Hayek’s Armani look in 1997, complete with a tiara.
See these and more of Vogue’s votes for the best Oscars dresses below.
Photo: Getty Images1/66Rihanna in Alaïa, 2023
Leave it to Rihanna to deliver one of the most stylish maternity looks in Oscars history. Her bodycon Alaïa featured just the right amount of sheerness—and the leather accents made her otherwise-classic silhouette feel totally modern.— Christian Allaire, Vogue Senior Fashion and Style Writer
Photo: Getty Images2/66Gemma Chan in Valentino, 2019
It’s a statement, it’s couture, it looks comfortable, and it has pockets!— Lucie Zhang, former Vogue Associate Director, Social Media
Photo: Getty Images3/66Mila Kunis in Elie Saab, 2011
I remember being so awestruck by Mila Kunis in this lavender Elie Saab dress at the 2011 Oscars. Between the strategic lace paneling and the gorgeous draping, it was a total showstopper in my book. Plus it’s a great color on her!— Hannah Jackson, Vogue Fashion Writer
Photo: Getty Images4/66Julia Roberts in Valentino, 2001
I’ll never forget it and neither has the fashion world: Julia Roberts in her vintage Valentino gown for her first-time Oscars win for Erin Brockovich. The black and white, velvet and satin Valentino gown was classic and elegant then—and it’s still timeless today.— Julie Tong, former Vogue Commerce Editor
Photo: Getty Images5/66Sharon Stone in Vera Wang and Gap, 1998
There is fashion, and there is style. When Sharon Stone hit the red carpet in a crisp white button down and evening skirt, she proved to have the latter in spades. That she was able to respect the formality of the dress code in rolled-up sleeves is truly a wonder—though the diamond bracelets certainly helped!
—Leah Faye Cooper, former Vogue Digital Style Director
Photo: Getty Images6/66Lauren Hutton in Halston, 1975
Lauren Hutton in Halston with a huge fur on top! Needs no explanation!—Catherine Piercy, former Vogue Beauty Director
Photo: Getty Images7/66Regina King in Louis Vuitton, 2021
Regina King opted for a bold silhouette in Louis Vuitton—and the risk-taking move totally paid off. The jaw-dropping dress took over 62,000 sequins, 3,900 crystals, and 140 hours to produce.—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images8/66Natalie Portman in Dior, 2020
Natalie Portman and Dior is already a winning combination, but for the 2020 Oscars, she raised the bar for award show fashion with a powerful statement. She wore a Dior gown with a matching cape embroidered with the names of snubbed female directors. Fashion, but make it feminist! — Clarissa Schmidt, former Vogue Associate Producer
Photo: Getty Images9/66Grace Kelly in Edith Head, 1955
The celadon satin gown that Grace Kelly wore to collects her 1955 Oscar for The Country Girl will always be my all-time favorite. And designed by Edith Head, no less!—Chloe Malle, Vogue Head of Editorial Content
Photo: Getty Images10/66Zendaya in Valentino Couture, 2022
Zendaya pulled off one of the most unexpected ensembles of the evening in her Valentino Couture look: She balanced a cropped white button-up shirt with a silver sequined skirt. It felt simultaneously modern and classic at the same time—a new take on Old Hollywood glamour.—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images11/66Uma Thurman in Bottega Veneta, 2022
I love this Uma moment in Matthieu Blazy’s Bottega Veneta. In hindsight, this look very much encompasses his work at the label so far: Effortlessly sophisticated, while still thoughtful and considerate. To me, this was giving pure self-assured elegance, the kind only a woman with Uma's trajectory could emanate. So chic. I also loved that this felt reminiscent of the Vera Wang silk skirt and Gap button-down that Sharon Stone wore to the Oscars in 1998 (which is another favorite of mine). —José Criales-Unzueta, former Replica Handbag Store Runway Fashion News Writer
Photo: Getty Images12/66Charlize Theron in Gucci, 2004
Charlize Theron’s glittering silver Gucci gown is a prime example that less is often way more on the red carpet. Despite its simple shape, it’s one of the Oscars’s most memorable dresses in history: you can thank its flawless fit for that. When Theron went on to collects her Best Actress trophy for Monster that year, she definitely looked the part of a true Hollywood movie star.—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images13/66Cher in Bob Mackie, 1974
Cher has had her fair share of iconic Oscars looks. Whether it’s the golden bejeweled Bob Mackie two-piece set that she wore to the 1973 ceremony or the ornate black gown that she wore to the Academy Awards in 1986 (also a Mackie creation), which really seemed like more of an excuse for her to wear that matching, massive, spiky jewel-encrusted headpiece on her head, she’s always walked that esteemed red carpet in something truly memorable. But it’s the 1974 Mackie-designed look that I feel has retrospectively gotten less attention than is deserved—it’s a watercolor-esque print of pastel colors on a flattering tube top of sorts, with a matching, flowing skirt. Cher finished off the look with matching eyeshadow, a sparkly flower neckpiece, and, of course, a headpiece.—Rachel Hahn, former Vogue Fashion News Writer
Photo: Getty Images14/66Marion Cotillard in Jean Paul Gaultier, 2008
To this day, Marion Cotillard in Jean Paul Gaultier Couture at the 2008 Oscars is one of my favorite fashion moments of all time. Winning for Best Actress for her portrayal of Edith Piaf in La Vie en Rose, it was her big moment—and her gown couldn’t have suited it more perfectly. The form-fitting fishtail shape was both sexy and demure at the same time, and the intricate scallop detail was just so beautiful. I also love how she layered on the golden, navel-grazing strand necklaces. Such a cool laissez-faire touch.—Lauren Valenti, Vogue Senior Beauty Editor
Photo: Getty Images15/66Martha Plimpton in vintage, 1989
When a plus-one outshines them all…Martha Plimpton in a vintage cream satin bias-cut dress in 1989—Old Hollywood elegance but somehow capturing a pre-grunge coolness (best accessory: River Phoenix). Uncontrived and charming.—Emma Elwick-Bates, former Vogue Contributor
Photo: Getty Images16/66Cate Blanchett in Givenchy Couture, 2011
I remember the first time I saw the Givenchy Spring 2011 Haute Couture collectsion so well; shown inside the gilded Place Vendôme, the gowns’ juxtaposition of soft falling textures and armor-like tailoring evoked the terrifying beauty of angels. In this lilac and chartreuse look, Cate Blanchett simply confirmed that impression.—Estelle Tang, former Vogue Senior Culture Editor
Photo: Getty Images17/66Lupita Nyong’o in Prada, 2022
Lupita Nyong’o nodded to the iconic gold Oscars statue with her very own golden Prada gown, complete with quarter-length sleeves and a swishy fringed skirt.—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images18/66Tessa Thompson in Chanel Couture, 2019
I loved Chanel’s new interpretation of a classic column gown that Tessa Thompson wore to the 2019 Oscars. Its sequin panels and subtle ruffles added a little bit of fun to the classic LBD. — Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images19/66Audrey Hepburn in Givenchy, 1975
While Audrey Hepburn is best known for her gamine style through the 1950s (think: Funny Face and Roman Holiday) her ’60s and ’70s style has a permanent place on my mood board for its playful sophistication. This gown is just beautiful, and by her longtime collaborator Givenchy. You wouldn’t think midriff cutouts and Audrey Hepburn would go together, but the effect is just stunning. — Sarah Spellings, former Vogue Fashion News Editor
Photo: Getty Images20/66Jessica Alba in Versace, 2006
I remember seeing this dress growing up and feeling stunned. Looking at it now, I still feel that way. It’s such a timeless dress that elegantly accentuates her figure. The details on the bottom half of the dress are subtle and beautiful. I love that she paired it with minimalist jewelry (I’m an earring girl!) and a classy updo. The color makes her look like she’s glowing—a ray of sunshine. I love pieces that I can move around freely in, but are still form-fitting without being too constricting at the same time. This looks like one of those dresses. I hope to one day have a reason to wear a dress like this!— Akili King, former Vogue Beauty Assistant
Photo: Getty Images21/66Jane Fonda in Yves Saint Laurent, 1972
Jane Fonda at the 1972 Academy Awards where she won Best Actress for Klute. In the spirit of those similarly dystopian days of Vietnam and Nixon, she wore a black wool Yves Saint Laurent couture tunic and pantsuit (from her Roger Vadim Paris days) with the shag haircut of her call girl character, Bree, in the movie. Perfection and enduringly modern and makes today’s prom mermaids look like, well, prom mermaids. Mum, a Fonda fanatic, had that same haircut and gave them to my sister and I.
—Hamish Bowles, Vogue Editor at Large
Photo: Getty Images22/66Gwyneth Paltrow in Tom Ford, 2012
Gwyneth Paltrow in Tom Ford at the 2012 Academy Awards: immaculate and uncluttered, and straight from Marge Sherwood’s steamer trunk.—Jane Chun, Vogue Copy Chief
Photo: Getty Images23/66Kirsten Dunst in Christian Lacroix, 2022
Kirsten Dunst embraced vintage style at the 2022 Oscars, when she wore a strapless Christian Lacroix gown from its fall 2002 couture collectsion. The tiered ruffles and bright pink hue felt just as fresh and modern two decades later.—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images24/66Zendaya in Valentino, 2021
Zendaya rarely misses on any step and repeat, but her 2021 Oscars dress is one of her all-time best. The arresting yellow hue is a statement alone, but I love that she opted for a modern take on the classic, floor-length gown via a tasteful cutout. The design felt fresh and fun, and the perfect balance between glamour and ease.—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images25/66Salma Hayek in Armani, 1997
Salma Hayek in Armani, complete with a tiara. A modern day princess.—Puja Prakash, Vogue Senior Manager, Social Media
Photo: Getty Images26/66Jennifer Lawrence in Christian Dior Couture, 2013
Jennifer Lawrence’s Dior Couture in 2013 was like a fantasy wedding dress, and the delicate necklace she wore down her back was so feminine and fresh. Yes, she fell going up the stairs to accept the big prize, but boy did she look fabulous.—Alexandra Macon, Vogue Contributing Living Editor
Photo: Getty Images27/66Winona Ryder in Chanel, 1997
Winona Ryder in Chanel in 1997—because she was and is the coolest thing in town and there is such a sartorial nonchalance about her.—Elisabeth von Thurn und Taxis, Vogue Style Editor at Large
Photo: Getty Images28/66Céline Dion in Christian Dior, 1999
I love the pre-stylist, who-gives-an-eff-about-the-worst-dressed-list era of the Oscars—before everyone wore boring, perfect, off-the-shoulder mermaid dresses. In this sphere, nothing beats Björk’s swan dress, or Céline Dion’s backward tuxedo and top hat. But in more sane choices that still felt iconic and daring, Nicole Kidman’s Galliano for Dior in 1997: The color, the neckline, and the way she towered over Tom Cruise cannot be beat.—Michelle Ruiz, Vogue Contributing Editor
Photo: Getty Images29/66Amanda Seyfried in Giorgio Armani, 2021
Designed by Giorgio Armani himself, Amanda Seyfriend's dramatic, red tulle creation was inspired by hibiscus flowers. It continued her winning streak of classic, Old Hollywood style that she had been embracing all awards season long.
—Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images30/66Janelle Monáe in Ralph Lauren, 2020
Janelle Monáe is one of those stars that can pull off just about any silhouette or color on the red carpet, and who better to rock this sequined (and caped!) Ralph Lauren gown than her? I love that it’s super unconventional—and even a little futuristic—yet somehow it still reads as super glamorous. —Christian Allaire, Vogue Fashion & Style Writer
Photo: Getty Images31/66Björk in Marjan Pejoski, 2001
When Björk wore Marjan Pejoski’s Swan dress to the 2001 Oscars, Joan Rivers said, “This girl should be put in an asylum”—but I don’t think she was the slightest bit crazy. Although, maybe leaving those ostrich eggs on the red carpet was a little eccentric.
—Luke Leitch, Vogue Contributing Editor
Photo: Getty Images32/66Billy Porter in Christian Siriano, 2019
When I first saw Billy Porter's 2019 Oscars look, I was floored. It was neither a tuxedo nor a gown, but an actor showing up as themselves in a grandiose way. A true iconic moment in Oscar history. — Cassandra Pintro, former Vogue Editorial Producer
Photo: Getty Images33/66Lupita Nyong’o in Prada, 2014
I’m not the kind who subscribes to the notion of Disney princess red carpet moments, but there was something truly magical about the Prada dress that Lupita Nyong’o wore to the Oscars in 2014. First off, the pale sky blue color was such a great match for the actress, and a shade you don’t see too often in Hollywood. The silhouette was pretty special, too; seeing Nyong’o climb the steps to receive her award with a trail of pleated silk chiffon behind her was amazing. I had been rooting for her all season long, and the fact that she seemed to be poised and at ease in the dress made the moment extra special—the tiara was a nice finishing touch as well. It was just the right look for such a historic moment.—Chioma Nnadi, British Vogue Head of Editorial Content
Photo: Getty Images34/66Viola Davis in Armani Privé, 2017
Viola Davis’s 2017 Oscar win spoke volumes about the direction of cinema—her red Armani Privé gown spoke even louder. She was a force to be reckoned with in every step, a true vision. — Cassandra Pintro, former Vogue Editorial Producer
Photo: Getty Images35/66Faye Dunaway in Theadora Van Runkle, 1968
Faye Dunaway’s Oscars outfit in 1968. I don’t even know if it’s a dress or a coat, but I love anything with a feather-y trim.
—Nikola Jocic, former Vogue Graphic Designer
Photo: Getty Images36/66Elsie Fisher in Thom Browne, 2019
When I think about my favorite Oscars outfits, I’m really thinking about how happy—or unhappy—I’d be if it were me wearing them down the red carpet on Hollywood’s biggest night. That’s probably why I loved Elsie Fisher’s Thom Browne suit from 2019; it’s polished, it’s classic, and she looks like a lil’ baby Margot Tenenbaum with her barrette and purse. Most of all, though, she looks comfortable, which is exactly what I would have wanted to project if I had been the one attending the Oscars at 15 (perish the thought).— Emma Specter, Vogue Culture Writer
Photo: Getty Images37/66Halle Berry in Elie Saab, 2002
My obsession with Oscars fashion begins with Halle Berry in this Elie Saab gown at the 2002 Academy Awards. There’s just something so iconic and powerful about the dress—from the shape to the detailed embroidering, it remains my absolute favorite. And the fact that she wore it while accepting Best Actress, the first Black woman to win that category, just makes it all the more iconic.— Atalie Gimmel, former Vogue Associate Manager, Social Media
Photo: Getty Images38/66Michelle Williams in Vera Wang, 2006
Michelle Williams in canary yellow Vera Wang at the 2006 ceremony goes down as best dressed in my book. On paper, everything about that color and the dress’s complicated draping should be wrong, but Williams pulled it off like a champ, finding the perfect shade of deep red lipstick to complement her dress. I also have to call out Scarlett Johansson at the 2005 Oscars, who topped off her simple black Roland Mouret dress with a tiara. Both looks edge more editorial, which is why I like them over the standard fare you typically see at the Oscars. I remember growing up, watching both red carpets and thinking Williams and Johansson looked like they stepped out of the pages of Vogue (specifically, the February 2004 issue with Natalie Portman on the cover with her new ’20s bob).—Steff Yotka, former Vogue Fashion News and Emerging Platforms Editor
Photo: Getty Images39/66Nicole Kidman in Balenciaga, 2007
Nicole Kidman’s cherry red Balenciaga gown from 2007! It still looks so modern and elegant. Someone could wear it this year and you’d never guess it was 11 years old. And I love anything with a bow!
—Emily Farra, former Vogue Fashion News Writer
Photo: Getty Images40/66Angelina Jolie in Marc Bouwer, 2004
Angelina Jolie can do no wrong in my book. Her leg-baring moment in Atelier Versace in 2012 was one of her most buzz-worthy red carpet looks, while her 2014 Elie Saab Couture dress was a lesson in mildly sheer elegance, but her best look of all time has to be the Marc Bouwer in 2004. In the most unforgiving combination of satin and white, it hugged her curves in all the right places with the right amount of décolletage revealed—Hollywood glam at its best.—Christina Liao, Vogue Contributor
Photo: Getty Images41/66Zendaya in Giambattista Valli Haute Couture, 2018
Brown is perhaps the trickiest color to pull off on a red carpet, but leave it to Zendaya to make it ultra-glam. I love the gown's asymmetrical sleeve and soft draping. Super timeless and elegant. — Christian Allaire, Replica Handbag Store Fashion & Style Writer
Photo: Getty Images42/66Lupita Nyong'o in Calvin Klein Collection, 2015
She’s dripping pearls—that’s the tea! Despite the fact that this gown was probably very heavy, I love its streamlined shape, which fits her to perfection. The unfussy design makes the texture of the pearls shine. And boy, did she ever shine that night! — Christian Allaire, Replica Handbag Store Fashion & Style Writer
Photo: Getty Images43/66Hilary Swank in Guy Laroche, 2005
Business in the front, party in the back! That was the message behind the Guy Laroche dress Hilary Swank wore in 2005. The midnight blue hue was a cool alternative to black, and the derriere-skimming backless design made for a strong statement from every angle. Nominated for her role in Million Dollar Baby (for which she took home the Best Actress statue that night), a perfectly chiseled Swank proved that cleavage isn’t the only way to flash some skin on the Oscars red carpet. —Maria Ward, former Vogue Fashion News Writer
Photo: Getty Images44/66Diahann Carroll, 1969
The image of Diahann Carroll wearing this blush gown and glorious, jewel-adorned cape in 1969 will forever be my favorite Oscar moment. To me, she is the epitome of elegance, glamour, and regality. — Alexis Bennett, former Vogue Commerce Writer
Photo: Getty Images45/66Anjelica Huston in Halston, 1975
Halston and the 1975 Oscars made for quite the match. Anjelica Huston—on the arm of Jack Nicholson—seemed like a modern-day mermaid in a fish scale–patterned iridescent number by the designer, while Lauren Hutton paired a pastel-hued gown with a fur chubby and bare, bronzed skin—two looks that proved glamour and ease can, in fact, go hand in hand.
—Zoe Ruffner, former Vogue Associate Beauty Editor
Photo: Getty Images46/66Claire Danes in Cerutti by Narciso Rodriguez, 1997
I remember watching this! The bias-cut-skirt-plus-tee silhouette was an ultramodern take on ingenue dressing that still feels fresh (and ageless) today, and the color is just perfection—especially worn with matching eye makeup.
—Eviana Hartman, Vogue Contributing Editor
Photo: Getty Images47/66Cameron Diaz in Emanuel Ungaro Couture, 2002
I was struggling between Uma Thurman in fresh white Christian Lacroix (2004) and Cameron Diaz in Ungaro Couture (2002), and have decided on the latter, in part because of the Fred Leighton necklace/belt, but mostly because it’s refreshing to see glamour with a boho rather than a glitzy edge—not to mention that the easy beauty of this look jives with who I understand the actress to be.
—Laird Borrelli-Persson, Vogue Archive Editor
Photo: Getty Images48/66Uma Thurman in Prada designed by Barbar Tfank , 1995
A true ’90s minimalist princess moment. Need I say more?
—Anny Choi, former Vogue Market Editor
Photo: Getty Images49/66Nicole Kidman in Christian Dior Couture, 1997
One of the most iconic moments in fashion or red carpet history has to be Nicole Kidman in John Galliano’s chartreuse Christian Dior Couture dress in 1997. The elegant Asian-inspired silhouette and motif when paired with a frosted blue satin slingback and ladylike chinoiserie-inspired purse was the ideal combination. Kidman’s dress became the new benchmark in red carpet style, prompting countless others to make their mark in fashion-forward looks for years to come.
—Edward Barsamian, former Vogue Style Editor
Photo: Getty Images50/66Reese Witherspoon in vintage Christian Dior, 2006
This was the year she won Best Actress for her role in Walk the Line, and she really shone all night, from the red carpet to the stage. And while it’s a far cry from anything Legally Blonde, I love that the ribbons on the dress still have a hint of pink.
—Ella Riley-Adams, former Vogue Living Editor
Photo: Getty Images51/66Barbra Streisand in Arnold Scaasi, 1969
In a sea of princess gowns and Grecian flou, it’s hard to imagine anything chicer than turning up in a sheer sequined suit on the red carpet. Barbra Streisand’s winning 1969 Academy Awards look (she picked up Best Actress, for Funny Girl) may have raised eyebrows at the time, but these days, the ensemble feels like proof that having fun with fashion—and standing out in a crowd—is always the best choice in the long run.
—Alessandra Codinha, former Vogue Culture Editor
Photo: Getty Images52/66Madonna in Olivier Theyskens, 1998
Madonna’s 1998 Oscars gown by Olivier Theyskens was the perfect balance of punk and Pre-Raphaelite allure. The look was cool, and even though it came with a corseted bodice and full taffeta skirt, Madge made it seem effortless.
—Brooke Bobb, former Vogue Fashion News Writer
Photo: Getty Images53/66Natalie Portman in vintage Christian Dior, 2012
The only thing better than Natalie Portman in a Christian Dior ball gown is Natalie Portman in a vintage Christian Dior ball gown. My heart skipped a beat when the actress graced the 2012 Oscars red carpet in a polka-dotted couture confection from the brand’s 1954 printemps-été collectsion. J’adior, indeed.
—Lilah Ramzi, Vogue Features Editor
Photo: Getty Images54/66Alicia Vikander in Louis Vuitton, 2016
Alicia Vikander accepted her first Oscar in a pale yellow Louis Vuitton gown that did suggest Belle from Beauty and the Beast, but reimagined by Nicolas Ghesquière with a few fun details: the slight bubble hem and the uneven rain of silver sequins falling diagonally down the skirt. She looked incredibly cool and thrilled to be wearing it—a killer combo.
—Monica Kim, former Vogue Fashion News Editor
Photo: Getty Images55/66Tilda Swinton in Lanvin, 2009
I respect and appreciate nothing more than a sartorial risk-taker, especially when on a main stage like the Oscars. Tilda Swinton always seems to go against the grain on the red carpet and one of my favorite boundary-pushing looks of hers was her 2009 appearance in Lanvin. Though some dubbed this look worthy of a “worst dressed” list, I found Swinton to look regal, elegant, and statuesque.
—Kirby Marzec, former Vogue Senior Market Editor
Photo: Getty Images56/66Michelle Williams in Louis Vuitton, 2012
It takes a certain kind of woman to do red right on the red carpet, and Michelle Williams is that woman. This vibrant Louis Vuitton peplum gown remains one of my favorites year after year—and matching a lipstick to your dress is always a yes in my book.
—Jenna Rennert, former Vogue Associate Beauty Editor
Photo: Getty Images57/66Winona Ryder in vintage, 1996
Winona Ryder in vintage at the 1996 Oscars was incredible. Few people do Old Hollywood glamour as well as Ryder, and her love of vintage often means that she’s wearing pieces from the eras she references. Her delicately beaded Champagne-hued gown would have been wonderful all on its own, but worn with marcel waves and diamonds, it was a flapper moment that remains one of her best.
—Janelle Okwodu, former Vogue Fashion News Writer
Photo: Getty Images58/66Jennifer Lawrence in Calvin Klein, 2011
Before there was Jennifer Lawrence of Die My Love, Red Sparrow, Mother!, or even Silver Linings Playbook, there was Jennifer Lawrence of Winter’s Bone—a small indie film that got the then-20-year-old actress her first Academy Award nomination. While many may want to make their Oscars debut with a splash, Lawrence donned a minimalistic, figure-hugging red dress instead. Its slinky simplicity made the whole look red-hot and showed that Lawrence was a sartorial star in the making.
—Elise Taylor, former Vogue Living Writer
Photo: Getty Images59/66Zendaya in Armani Privé, 2024
The star delivered a fresh new take on Old Hollywood dressing in her embroidered palm tree-print gown by Armani Privé. The gunmetal paillettes made the design feel retro, yet modern, and she accessorized it with striking Bulgari jewels.
—Christian Allaire, Vogue Senior Fashion & Style Writer
Photo: Getty Images60/66Jennifer Lawrence in Dior Couture, 2024
Once a Dior girl, always a Dior girl. Jennifer Lawrence exuded elegance in her polka-dotted strapless Dior Couture number, complete with the matching shawl. Her Swarovski jewelry also shimmed under the paparazzi flashes.
—Christian Allaire, Vogue Senior Fashion & Style Writer
Photo: Getty Images61/66Lily Gladstone in Gucci, 2024
Always one to spotlight Indigenous fashion on the red carpet, Lily Gladstone sported an intricate Gucci gown that was made in collaboration with master quillwork artist Joe Big Mountain—a renowned artist within the Native American fashion space. It was the perfect balance of traditional craft with modern flair.
—Christian Allaire, Vogue Senior Fashion & Style Writer
Photo: Getty Images62/66Carey Mulligan in Balenciaga, 2024
At the 2024 Oscars, the star wore a recreation of a classic Balenciaga design from 1951—yet the strapless silhouette and scalloped mermaid hemline felt just as fresh and modern today.
—Christian Allaire, Vogue Senior Fashion & Style Writer
- Photo: Getty Images63/66
Mikey Madison in Dior, 2025
First-time nominee, first-time best actress winner Mikey Madison had established a super feminine, ladylike sensibilities across 2025’s awards ceremony circuit. It was only right that she crowned the season in this sugary pink, bow-waisted Dior gown with an undulating train. Old Hollywood, but still youthful and fresh—Anna Cafolla, Vogue News Editor
Photo: Getty Images64/66Michelle Yeoh in Balenciaga, 2025
We’ve gone all-in on jewel tones, but Michelle Yeoh was very much an early adopter in this Mattise blue Balenciaga gown. Elegant with its artful draping and unfurling train, the addition of a diamond-encrusted Boucheron ear cuff was pure class.—Anna Cafolla, Vogue News Editor
- Photo: Getty Images65/66
Elle Fanning in Givenchy by Sarah Burton, 2025
Elle Fanning was the first to wear Burton’s iteration of Givenchy, and it certainly made a statement. Inspired by a 1952 archival design, this custom haute couture look ushered in a new era for the storied French house, delighting in a stripped back but supremely feminine sense of modernity. The white French Lyon lace and black grosgrain bow is pretty and sweet, but the corseted bodice and fluffed-up cape gave it a contemporary spark.—Anna Cafolla, Vogue News Editor
Photo: Getty Images66/66Ariana Grande in Schiaparelli, 2025
The good witch Glinda at the height of her powers—helped by over 190,000 pink crystals, no less. This Schiaparelli dress, with its shapely peplum and gauzy tulle skirt, felt just the right amount of whimsical without sacrificing the wow factor. Method dressing, yes, but also one of her most experimental and avant-garde looks to date.—Anna Cafolla, Vogue News Editor
More on the 2026 Oscars
