15 Most Memorable Fashion Looks at the Oscars

6:16 PM 2/9/2020

by Lindsay Weinberg

Billy Porter, Scarlett Johansson, Cynthia Erivo and Florence Pugh top off the list of well-dressed stars at the Oscars.

Billy Porter, ScarJo, Cynthia Erivo and Florence Pugh - Getty - Split - H 2020
Getty Images

Pink proved to be the color of the night at the 2020 Academy Awards, with Little Women's Laura Dern, Parasite's Park So-Dam, Once Upon a Time in Hollywood's Julia Butters and presenters Regina King and Brie Larson donning blush and bright pink tones. 

Nominated actresses trended toward a polished black-and-white color palette — including Charlize Theron (in Dior Haute Couture), Renée Zellweger (in Armani Prive) and Cynthia Erivo (in Versace). Meanwhile, the Little Women stars brought bold colors or fresh silhouettes to the carpet, such as Saoirse Ronan's peplum Gucci, Florence Pugh's tiered Louis Vuitton and director Greta Gerwig's olive green Dior.

Though Mahershala Ali and Rami Malek were sleek as always in Ermenegildo Zegna XXX and Yves Saint Laurent, respectively, a few men dared to experiment beyond a black tux. Namely, Billy Porter donning another gown, Spike Lee honoring Kobe Bryant and Timothee Chalamet ditching the tuxedo for an upscale Prada jogging suit. 

Even singer Billie Eilish swapped out her street style for a custom, elevated white Chanel suit, accessorizing with plenty of glittering logo brooches. 

Here are the 15 most memorable looks on the 2020 Oscars red carpet, ranging from Janelle Monae's crystal-encrusted, hooded gown to Penelope Cruz's elegant Chanel dress.

  • Billy Porter

    Reminiscent of a fiery phoenix, Billy Porter upped the anti on his Oscars look following his tuxedo gown by Christian Siriano last year. This time, Porter donned a dress by Giles Deacon, inspired by the Cupola Room at Kensington Palace and featuring a 24-karat gold feathered top and painterly orange silk skirt. Stylist Sam Ratelle topped it off with powerful golden platform boots by Jimmy Choo. 

  • Cynthia Erivo

    "She wanted white," stylist Jason Bolden wrote on Instagram of Erivo's custom Versace gown with embellished bodice and mesh detail. The best actress nominee for Harriet pulled off an Angelina Jolie moment with her high slit and added bling with Maria Tash earrings and rings.

  • Scarlett Johansson

    The double nominee brought the sultry glamour with a silky, custom Oscar de la Renta dress with a deconstructed corset waist and draped silver strands. She sparkled in one-of-a-kind 27-carat diamond earrings designed by Anita Ko, which center on four Forevermark Exceptional diamonds. Each pear-shaped diamond is about six carats, completing the outfit styled by Molly Dickson.

  • Brie Larson

    Larson was stunning in an embellished, blush-toned Celine dress (with cape sleeves) comprising 120,000 sequins, 110,000 glass beads, 13,000 Swarovski crystals and 6,500 pink jewels, designed by Hedi Slimane. Her gown, styled by Samantha McMillen, took 1,200 hours to hand-embroider.

  • Florence Pugh

    The Little Women supporting actress nominee rocked a bold teal hue in her Louis Vuitton tiered gown, Goutte de Sang rings and necklace (starring a 21-carat imperial topaz), worn with her Maria Tash ear stud. "Baby girl's first Oscars," wrote stylist Rebecca Corbin-Murray on Instagram. 

  • Timothée Chalamet

    The red carpet trendsetter ditched the Louis Vuitton "bib" and instead opted for a casual bomber jacket, black boots and sleek trousers that were fitting for the rainy day (also note the wet hair look). The presenter and Little Women actor made a statement with a ruby and diamond Cartier brooch to complement his fashion-forward Prada ensemble. 

  • Charlize Theron

    Donning Dior for the ninth time at the Oscars, Theron went classic in an asymmetrical off-the-shoulder black gown with high slit and sweeping train. She let her Tiffany & Co gems do the talking — the 165 diamonds total 21 carats and are valued at $5 million. "How can something be so beautiful? A night like tonight calls for one-of-a-kind natural diamonds – it’s no wonder these precious gems have been synonymous with Hollywood for decades," wrote her stylist Leslie Fremar on Instagram.


  • Janelle Monae

    Monae channeled the Fairy Godmother in a structured hooded dress by Ralph Lauren — with an open back. She wore a Forevermark Lace of Light choker with 36.54 carats of diamonds to go with the custom silk lame tulle mesh dress. It took 600 hours to hand-embroider with 168,000 Swarovski crystals.

    "We were very inspired by afrofuturism and the idea of Janelle being a queen floating down from an intergalactic diamond planet, somewhere in the far reaches of the universe. We were also inspired by Prince and his incredible blue sparkle Oscar moment," says stylist Alexandra Mandelkorn. "It’s truly a masterpiece!"

  • Spike Lee

    After honoring Prince at last year's Oscars, Lee paid tribute to the late Kobe Bryant with a custom Gucci suit with "24" patches on the lapels and back that nodded to Bryant's basketball jersey numbers. He paired it with Strategy Nike Kobe 9 Elite orange sneakers and a cross necklace, dressed by BlacKkKlansman costume designer Marci Rodgers.

  • Regina King

    The presenter, who won for best supporting actress last year, returned to the Oscars in a blush Versace dress with a long train. She said it was the "first time I’ve had this much dress, but I think it works with the weather." The single-strap gown was paired with Harry Winston jewels, styled by Wayman Bannerman and Micah McDonald. 

  • Penelope Cruz

    The Pain and Glory actress unsurprisingly wore Chanel and Swarovski, as a face of both the French House and jeweler. Her elegant high-low silk dress featured a halter neck, pearl belt and tulle floral detail, all inspired by the Spring/Summer 1995 Haute Couture collection. Cruz was styled by Cristina Ehrlich with a Bespoke Atelier Swarovski Fine Jewelry ring with a 3.92 carat sustainably created diamond. 

  • Kaitlyn Dever

    Dever made a sustainable statement at the Oscars in an ethically made Louis Vuitton silk satin gown, embroidered with Swarovski crystals and glass beads. The crimson dress and shawl were part of Suzy Amis Cameron's eco-friendly campaign called Red Carpet Green Dress. "Go #sustainable but make it fucking #moviestar," wrote stylist Karla Welch on Instagram.

  • Billie Eilish

    Eilish, performing at the Oscars, brought her signature designer logo aesthetic to the red carpet. Instead of her neon green Gucci vibe from the Grammys, the "Bad Guy" singer opted for a white Chanel tweed suit inspired by the Fall/Winter 2019-2020 collection.

    Eilish and stylist Samantha Burkhart accessorized with two gold lion rings; several double C brooches; a colorful hair scarf; earrings that spelled out "Chanel" and matching fingerless gloves. She ditched the usual dark sunglasses and face mask, perhaps keeping it a bit more traditional for the Academy Awards. 

  • Saoirse Ronan

    Styled by Elizabeth Saltzman, the best actress nominee was a chic Ursula in a black peplum top and lavender skirt ensemble by Gucci (with blonde bangs!). The black fabric is the same as that of her Gucci dress from the BAFTAs in a nod to sustainability. 

  • Renée Zellweger

    Nominated for best actress for Judy, Zellweger ended her colorful awards season with a return to white: a single-shoulder Armani Prive column dress with a David Webb ring, styled by Petra Flannery.