Janelle 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
Audrey 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, Vogue Fashion News Editor
Gemma Chan in Valentino, 2019
It’s a statement, it’s couture, it looks comfortable, and it has pockets!
— Lucie Zhang, Vogue Associate Director, Social Media
Billy 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, Vogue Editorial Producer
Tessa 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
Julia 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, Vogue Commerce Editor
Jessica 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, Vogue Beauty Assistant
Charlize 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 collect 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
Grace Kelly in Edith Head, 1955
The celadon satin gown that Grace Kelly wore to collect her 1955 Oscar for The Country Girl will always be my all-time favorite. And designed by Edith Head, no less!
—Chloe Malle, Vogue Contributing Editor
Lupita 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, Vogue Fashion News Director
Marion 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
Lauren Hutton in Halston, 1975
Lauren Hutton in Halston with a huge fur on top! Needs no explanation!
—Catherine Piercy, Vogue Beauty Director
Natalie 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, Vogue Associate Producer
Viola 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, Vogue Editorial Producer
Salma Hayek in Armani, 1997
Salma Hayek in Armani, complete with a tiara. A modern day princess.
—Puja Prakash, Vogue Senior Manager, Social Media
Cate Blanchett in Givenchy Couture, 2011
I remember the first time I saw the Givenchy Spring 2011 Haute Couture collection 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, Vogue Senior Culture Editor
Elsie 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
Jane 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 International Editor at Large
Halle 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, Vogue Associate Manager, Social Media
Michelle 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, Vogue Fashion News and Emerging Platforms Editor
Winona 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
Jennifer 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
Nicole 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, Vogue Fashion News Writer
Angelina 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 Contributo
Zendaya 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, Vogue Fashion & Style Writer
Hilary 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, Vogue Fashion News Writer
Faye 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, Vogue Graphic Designer
Björk 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
Cher 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, Vogue Fashion News Writer
Céline 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
Martha 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, Vogue Contributor
Diahann 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, Vogue Commerce Writer (edited)
Anjelica 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, Vogue Associate Beauty Editor
Claire 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
Cameron 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
Gwyneth 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
Uma Thurman in Prada designed by Barbar Tfank , 1995
A true ’90s minimalist princess moment. Need I say more?
—Anny Choi, Vogue Market Editor
Lupita Nyong’o in Calvin Klein Collection, 2015
She’s dripping pearls—need I say more? 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, Vogue Fashion & Style Writer
Reese 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, Vogue Living Editor
Barbra 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, Vogue Culture Editor
Madonna 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, Vogue Fashion News Writer
Natalie 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 collection. J’adior, indeed.
—Lilah Ramzi, Vogue Assistant Features Editor
Alicia 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, Vogue Fashion News Editor
Tilda 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, Vogue Senior Market Editor
Michelle 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, Vogue Associate Beauty Editor
Winona 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, Vogue Fashion News Writer
Jennifer Lawrence in Calvin Klein, 2011
Before there was Jennifer Lawrence of 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, Vogue Living Writer
Nicole 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, Vogue Style Editor
