The Academy Awards, more popularly referred to as the Oscars, honor film and thus bring out Hollywood’s biggest stars. But the ceremony has also become known for the fabulous fashion worn on the red carpet. Year after year, A-listers arrive in couture outfits that make for instantly memorable style moments.
The 98th ceremony, which is taking place at the Dolby Theatre in Los Angeles and streaming live on ABC and Hulu, will be the latest in the ceremony’s long evolution. What started as an industry insider event has morphed into a much larger and impressive spectacle. Historically, celebs turned up in reserved and muted evening-wear, but as more eyes have tuned into the red carpet, the fashions have become grander, bolder, and even downright iconic.
Take, for instance, Julia Roberts‘ black and white Valentino dress (in which she won an Academy Award!), or Sharon Stone, who showed up in a white button-down from the Gap paired with a custom Vera Wang skirt. Who can forget Halle Berry’s sheer Elie Saab gown, which she wore for her history-making win as the first Black actress to take home the Best Actress award in 2002? Or in 2024, when Lily Gladstone wore a Gucci dress that was made in collaboration with Indigenous artist Joe Big Mountain, featuring quillwork to honor her heritage? And that’s just scratching the surface!
So, as we wait excitedly to see what glorious fashion is in store for us this year, we’ve ranked our favorite looks from decades past to the present. Ahead, InStyle’s picks for the 40 best Oscar looks of all time.
Grace Kelly, 1956
Grace Kelly at the 1956 Oscars, her last appearance.
Getty
This was Grace Kelly’s final Oscar appearance before she left Hollywood to marry Prince Rainier of Monaco. Kelly, who had won the Best Actress Oscar the year prior for Country Girl, presented at the ceremony. Like many of her dresses, this floral gown was designed by Edith Head. Kelly’s most famous Oscars gown is the blue Edith Head dress she’d worn the year before, but this was a more regal, refined look for the soon-to-be royal.
Audrey Hepburn, 1965
Audrey Hepburn at the 1965 Oscars in a simple pink gown.
Getty
Audrey Hepburn helped to elevate Oscars style, bringing in elegant dresses by couture designers. Each of her appearances was instantly iconic, but this simple white gown with matching gloves, clutch, and pumps is a particular standout. Hepburn was attending in support of My Fair Lady, and it was a more sophisticated look than the more girlish floral dress she’d worn over a decade prior, when she won Best Actress for Roman Holiday.
Barbara Streisand, 1969
Barbara Streisand at the 1969 Oscars in sheer black sparkles.
Getty
In 1969, Barbra Streisand caused quite a stir at the Oscars. She wore a gorgeous shimmering bell-bottom pantsuit designed by Arnold Scaasi — but she hadn’t realized the material would become transparent under the stage lights. So when she took the stage to accept the Best Actress win for Funny Girl, she didn’t realize just how sheer the outfit looked.
Elizabeth Taylor, 1970
Elizabeth Taylor presenting at the 1970s Oscars in lilac and diamonds.
Getty
Elizabeth Taylor was as stylish as she was scandalous, and this outfit managed to embody both concepts perfectly. The low-cut periwinkle blue gown by Edith Head complemented Taylor’s infamous violet eyes, and the deep neckline was designed to show off the 69.42-carat “Taylor-Burton diamond”: Her husband at the time, Richard Burton, had purchased it for Taylor in 1969 for (reportedly) over a million dollars.
Raquel Welch, 1973
Raquel Welch in a strapless short gown at the 1973 Oscars.
Getty
Raquel Welch brought her signature va-va-voom and fashion-forward style to the Oscars, with low necklines, high slits, and daring silhouettes, during a time when the ceremony dress code was much more (literally) buttoned-up. This strapless, flowy gown recalls Golden Age Hollywood style with a more ’70s-appropriate update.
Anjelica Huston, 1975
Anjelica Huston and Jack Nicholson at the 1975 Oscars.
Getty
Anjelica Huston wore a gorgeous fish scale-patterned dress designed by Halston that she paired with a clutch and long necklace. It was ’70s-era perfection: Huston gave off iridescent mermaid-esque vibes. On her arm was, of course, her boyfriend at the time, Jack Nicholson, looking dapper and suave.
Diane Keaton, 1976
Diane Keaton in a white suit and striped shirt with a polka-dotted tie.
Getty
Diane Keaton will forever be a fashion icon because she dressed like herself regardless of the context — in this case, the 1976 Oscars. This white Richard Tyler suit was an early indicator of Keaton’s lifelong love of suiting, with the striped shirt and polka-dotted tie demonstrating her appreciation for stark, clashing patterns and textures.
Lauren Hutton, 1980
Lauren Hutton in a gold mini at the 1980 Oscars.
Getty
Lauren Hutton was a trendsetter in more ways than one. Arriving at the 1980 Oscars, the supermodel wore a golden Zoran minidress and sky-high black stilettos — something that wouldn’t be out of place at a party or a nightclub. It would be an early sign of the decade’s joyful experimentation and boundary-pushing, including at Hollywood’s biggest night.
Cher, 1986
Getty Images
Leave it to Cher to embrace “naked dressing” decades before it took hold of TikTok. This music legend earned her place in the pantheon of memorable Oscars looks with this ab-baring creation from her longtime collaborator Bob Mackie. Her black sequin-encrusted bralette, low-rise skirt, thigh-high boots, and enormous feathered headdress were quite a rebellious style statement.
Cindy Crawford, 1991
Ron Galella/Getty Images
Supermodel and fashion muse Cindy Crawford appeared on the arm of Pretty Woman star and future husband Richard Gere at the 1991 Oscars red carpet. Crawford’s fitted, flaming red Versace gown with a plunging neckline showcased her statuesque figure and ushered in an influx of dupe designs over the years.
Winona Ryder, 1994
Ron Galella/Getty Images
In 1994, Winona Ryder wore this vintage Edward Sebesta flapper-style, fringed slip dress that was heavily beaded and fit her like a glove. Her close-cut hair was a nostalgic nod to the Roaring ’20s.
Sharon Stone, 1998
Ke.Mazur/WireImage
Basic Instinct star Sharon Stone practically invented high-low dressing on the red carpet when she wore a crisp white button-down shirt from the Gap with a violet silk Vera Wang skirt. Stone proved that even off-the-rack pieces can look impossibly chic with the right styling.
Gwyneth Paltrow, 1999
Ke.Mazur/WireImage
Shakespeare in Love actress Gwyneth Paltrow personified the minimalism of the ‘90s with this bubblegum pink taffeta Ralph Lauren evening dress. Paltrow’s look featured clean lines and minimal makeup, letting her natural beauty and Harry Winston jewels shine.
Angelina Jolie, 2000
Ke.Mazur/WireImage
Angelina Jolie won a Best Actress Oscar in 2000 for her role in Girl, Interrupted. On the red carpet, she channeled an elegant Elvira in a black form-fitting frock from Marc Bouwer. Her pin-straight siren hair added to the gothic vibe of the dress.
Michelle Yeoh, 2001
Getty
In 2001, Michelle Yeoh attended the Academy Awards as a presenter in a show-stopping, hand-beaded Barney Cheng gown, inspired by Yeoh’s hit film, Crouching Tiger, Hidden Dragon (which was nominated for Best Picture that year). The Hong Kong–based designer chose a silhouette that nodded to Yeoh’s Asian heritage; combined with a thigh-high slit and elegant train, the overall effect was equal parts sexy and sophisticated. Later, in an interview with Harper’s Bazaar, Yeoh reminisced about wearing the look, saying it was “heavy…but you are walking on air because you’re at the Oscars.”
Julia Roberts, 2001
Kevin Winter/Getty Images
First modeled by supermodel Christy Turlington in 1992, this Valentino couture dress that Julia Roberts wore in 2001 is widely considered one of the most iconic Oscar looks. The floor-length black gown featured a white stripe that split at the bust to form straps and then weaved together in the back, giving way to a fanned tulle train.
Halle Berry, 2002
Steve Granitz/WireImage
Monster’s Ball actress Halle Berry made history in 2002 when she became the first woman of color to receive the Oscar award for Best Actress. For the historic occasion, Berry wore a romantic Elie Saab look that featured a revealing sheer bodice embellished with floral appliqué wrapped in a mauve red taffeta evening skirt.
Jennifer Lopez, 2003
J. Vespa/WireImage
J.Lo channeled Jackie O in this retro mint green Valentino gown and Harry Winston jewels in 2003. The one-sleeved caftan-style dress featured lavish floral embroidery at the sleeve, which continued down its layered skirt.
Charlize Theron, 2004
KMazur/WireImage
While she may have won the Best Actress award in 2004 for going under a major “make-under” for her murderous role in Monster, Charlize Theron showed up on the red carpet in full old-school Hollywood glam in this glittering Tom Ford for Gucci gown.
Hilary Swank, 2005
Million Dollar Baby star Hilary Swank looked like a million bucks in this navy long-sleeved dress from French fashion designer Guy Laroche. The deceptively simple look featured intricate pleating which wrapped around Swank’s torso and hips, and when the actress turned, the dress revealed her sculpted, bare back.
Keira Knightley, 2006
Vince Bucci/Getty Images
Stylist to the stars Rachel Zoe helped solidify British actress Keira Knightley’s red carpet icon status with this custom one-shoulder Vera Wang gown. Knightley’s merlot-hued taffeta gown and brilliant Bulgari necklace had us drunk in love with the look.
Nicole Kidman, 2007
Frazer Harrison/Getty Images
Nicole Kidman matched the red carpet in 2007 with this sleek and chic Balenciaga gown designed by Nicholas Ghesquière. The crimson-colored halter dress featured a floor-sweeping bow at the back of the neck that trailed behind Kidman as she walked by.
Marion Cotillard, 2008
Frazer Harrison/Getty Images
While she may have played singer Edith Piaf onscreen, on the Oscar red carpet French actress Marion Cotillard channeled a glamorous mermaid in a custom couture Jean Paul Gaultier white gown, which was covered in a sequined scale design.
Anne Hathaway, 2009
John Shearer/WireImage
Rachel Getting Married star Anne Hathaway looked pretty in this elegant, strapless Armani Privé column dress adorned head-to-toe with pearlescent sequined paillettes. Hathaway’s closely cropped hair showed off her Cartier diamond earrings.
Zoe Saldaña, 2010
Kevin Mazur/WireImage
Why go simple when you can go deliciously bold? That was the mantra that Zoe Saldaña adopted at the 2010 Oscars when she walked out in a maximalist design from Riccardo Tisci of Givenchy. Her look comprised a champagne sequined strapless bodice combined with a periwinkle purple skirt made of layers of ruffled ombré tulle.
Natalie Portman, 2011
Jason Merritt/Getty Images
Nominated for her role in Black Swan, Natalie Portman tapped Kate and Laura Mulleavy of Rodarte, who also designed costumes for the film, to create her Oscars maternity gown. Portman’s beaded tassel Tiffany & Co. earrings were a perfect match for her berry-hued silk chiffon dress.
Octavia Spencer, 2012
Kevork Djansezian/Getty Images
Over the years, Japanese designer Tadashi Shoji has proven to be Spencer’s stylish secret weapon, as some of her best red carpet looks have been his creations. This custom ivory dress, which reportedly took thousands of hours to hand bead, made The Help star sparkle on her big night.
Jennifer Lawrence, 2013
Gregg DeGuire/WireImage
The Silver Linings Playbook actress and muse to Raf Simons made a bold statement on the red carpet in 2013 when she donned this Dior couture creation. The bridal white, fishtail-hemmed gown was covered in a floral brocade that gave the look a fairy tale finish.
Lupita N’yongo, 2014
Gregg DeGuire/WireImage
For her Oscars debut, 12 Years a Slave actress Lupita Nyong’o looked like a princess when she channeled Cinderella in this baby blue Prada gown. While it may have looked simple, the dress featured a navel grazing v-neckline, a low-cut back, and a flowing pleated skirt with crystal trim that elegantly flowed behind her as she walked the red carpet.
Jessica Chastain, 2015
Jason Merritt/Getty Images
Never one to disappoint on the red carpet, Zero Dark Thirty actress Jessica Chastain looked like an Old Hollywood bombshell in this midnight blue Givenchy gown. Its simple silhouette was exaggerated by a sequined bodice that also had a draped silk cowl neckline, which fabulously framed her diamond Piaget collar necklace.
Cate Blanchett, 2016
Frazer Harrison/Getty Images
Nominated in the Best Supporting Actress category for her role in Carol, two-time Oscar winner Cate Blanchett wowed on the red carpet, wearing a seafoam blue Armani Privé gown covered in beaded feather embellishments made to resemble flowers. She accessorized her look with priceless diamonds from Tiffany & Co.
Emma Stone, 2017
Steve Granitz/WireImage
In 2017, La La Land actress Emma Stone wore a gold gown designed by Riccardo Tisci of Givenchy. The flapper-inspired look, which featured an ornate bodice and tiered beaded tassels, was actually one of Tisci’s final designs for the brand before he stepped down as creative director.
Margot Robbie, 2018
Neilson Barnard/Getty Images
Before she embraced Barbiecore pink on the Oscars red carpet, Margot Robbie wore this angelic white Chanel dress in 2018. Crystal beaded bands draped down from two camellia appliques paired with a clear lucite evening bag gave the delicate look a modern edge.
Lady Gaga, 2019
Frazer Harrison/Getty Images
The 2019 Oscars were a major milestone for Lady Gaga, who received two nominations for Best Actress and Best Original Song. She won the latter, so she had to go full tilt on the red carpet. For the occasion, Gaga chose a black strapless gown with exaggerated hips and flared skirt from Alexander McQueen. She paired black leather opera gloves and a door knocker of a necklace from Tiffany & Co, which featured a yellow diamond stone known as the “Tiffany Diamond,” totaling 128.54 carats.
Cynthia Erivo, 2020
Amy Sussman/Getty Images
Cynthia Erivo made a stylish statement for her Oscars debut in 2020, wearing a custom white Atelier Versace one-shoulder bustier gown with a crystal mesh bodice and a thigh-high front slit that gave a peek at her toned legs and white Stuart Weitzman platform heels. As for jewelry, Erivo wore a mix of Piaget diamond rings and earrings, along with Maria Tash earrings.
Regina King, 2021
Chris Pizzello-Pool/Getty Images
As one of the evening’s hosts, multi-hyphenated talent Regina King wore an icy blue custom duchess satin Louis Vuitton dress. The futuristic gown featured flared-winged sleeves and scalloped hem embroidered with silver sequins and crystals, which took over 140 hours to complete.
Zendaya, 2022
Gilbert Flores/Getty Images
Zendaya took a page from Sharon Stone’s style book and gave it a modern twist for her 2022 Oscars look. While Stone wore a white button-down from the Gap, Zendaya went for a cropped silk number from Valentino that she wore with a slinky, silver sequined evening skirt. The shirt’s three-quarter sleeves were perfect for showcasing her stacks of Bulgari serpentine cuffs.
Cara Delevingne, 2023
Mike Coppola/Getty Images
The actress and model made a grand red carpet entrance in a ravishing rose colored dress from Elie Saab. Delevingne’s Bulgari diamond necklace was beautifully framed by the off-the-shoulder frock, which featured a giant shoulder bow affixed to a ruched bodice. Her skirt’s high leg slit added a bit of sultriness to the classic look.
Lily Gladstone, 2024
Mike Coppola/Getty Images
As the first Native American woman to be nominated for Best Actress, Lily Gladstone paid homage to her heritage by wearing a dress made in collaboration with Gucci creative director Sabato De Sarno and Indigenous artist Joe Big Mountain. The midnight blue velvet dress featured a fitted bodice and long cape embroidered with a white floral quillwork motif.
Demi Moore, 2025
Demi Moore in silver sequins at the 2025 Oscars.
Getty
For her nomination for The Substance, Demi Moore opted for a custom Giorgio Armani Privé gown with crystal embroidery, an exaggerated hip, and long train. The gown invoked the “sparkle” of her movie character Elizabeth Sparkle; Moore’s longtime stylist Brad Goreski told Vogue that the goal was elegant and sophisticated, with an “unexpected twist.”