Oscars Dresses From The 2020s That Are Destined To Be In The Red Carpet Hall Of Fame

The Oscars is arguably the most important night in Hollywood. It is the night in which the most talented actors, creatives, and filmmakers are honored for their work on a global stage. It is also one of the biggest nights for fashion — said Hollywood stars have the opportunity to dazzle on the red carpet before they hear the (often controversial) awards results. However, many attendees don't exactly wow us with their looks. In fact, there have been quite a few fashion fails over the course of the Oscars' 97-year-long run; the list of worst-dressed celebs in Oscars history doesn't lie. 

The 2020s have been a tumultuous time in the fashion world; trends come and go quicker than ever, not to mention the fact that most luxury fashion houses' creative directors have been playing a giant game of musical chairs since 2025. But, while the looks from the worst-dressed celebs of the 2026 Oscars should be forgotten, there are many modern Oscars dresses that will stand the test of time. Despite everything, some celebrities have managed to put together some of the most iconic Oscars red carpet looks of all time. 

Wearing a red gown on the red carpet is an awards show cliché. However, Amanda Seyfried turned the conventional red dress on its head at the 2021 Oscars. While a few gowns from the 2020 Oscars ended up on the list of the worst Oscars looks of all time, many actors came back with jaw-dropping ensembles just one year later. Seyfried donned a bold Armani Privé tulle gown, with a low neckline and dramatically flared hem. She went all-in on the vintage vibes with a classic red lip and and elegant updo.

Halle Berry has gone through a stunning style transformation over the course of her career. One thing that has remained steadfast is her dedication to looking amazing at the Oscars. At the 2025 ceremony, Berry wore a jaw-dropping Christian Siriano gown plated with reflective silver panels. Berry's mirrored dress showed off her fantastic figure, and its modest train gave the look an extra bit of drama. The actor wore her hair in a short bob, which allowed the gown to speak for itself without a flashy hairdo to distract from it.

When Anya Taylor-Joy floated across the 2024 Oscars red carpet, she solidified herself as one of the most iconic Dior ambassadors in recent history. The actor wore a gown based off of the classic Dior Venus dress; Taylor-Joy's gown featured a very old-school Dior petaled skirt, which was made modern with a silver and light gray color scheme. She let the dress shine by keeping her hair and jewelry simple and streamlined. All in all, Taylor-Joy's look was the epitome of Oscars elegance.

Zendaya rarely, if ever, misses on a red carpet. From her iconic Met Gala looks, to her many fantastic press tour outfits, Zendaya has gone through an iconic style evolution. At the 2022 Academy Awards, she scored yet another fashion win in custom Valentino. Zendaya shirked awards show convention in a cropped satin blouse and sweeping silver skirt. While her look drew comparisons to Sharon Stone, who wore a similar button-down shirt and floor-length skirt combo at the 1998 Oscars, we think Zendaya put the perfect modern twist on it. 

Ariana Grande gave Glinda the Good Witch energy at the 2025 Oscars. The singer-turned-actor swept across the red carpet in a Schiaparelli gown from the spring 2025 couture collection. Grande's sculptural gown featured a light pink peplum bodice and a flowing tulle skirt decorated with thousands of crystals. The dress is one of the most iconic Oscars looks in recent history; it's high fashion, glamorous, and the perfect choice to continue Ariana Grande's pattern of picking outfits that scream "Wicked." 

Naturally, both Cynthia Erivo and Ariana Grande have made the list of most iconic 2020s Oscars dresses. Erivo channeled "Wicked" vibes in 2025 with a dark green gown by Louis Vuitton. Erivo, who was nominated for Best Actress for her performance in the aforementioned film, leaned into her role as misunderstood villain Elphaba with exaggerated silhouettes; the gown featured a dramatic collar, Cinderella-esque skirt, and bow-shaped bustier. Throughout Cynthia Erivo's stunning hair transformation, her shaved head circa 2025 has become one of many styles that suits her perfectly.

Doja Cat lived up to her namesake at the 2025 Oscars in a floor-length leopard print gown. The singer — who performed at the ceremony that night in an equally stunning custom Swarovski dress — wore a gown designed by Balmain's then-creative director Olivier Rousteing, who was inspired by a vintage Balmain look from the 1950s, according to Vogue. The silhouette flattered Doja, emphasizing her curves perfectly. The singer brought the look to the 2020s by wearing her natural curly hair in a short blonde cut. 

While it isn't one of Teyana Taylor's spiciest fashion looks, the feathered gown she wore to the 2026 Academy Awards was certainly one of her best — not to mention one of the best Oscars looks of the 2020s. Taylor, who was nominated for Best Supporting Actress, glided across the red carpet in a chiffon Chanel gown decorated with black and white feathers and gemstones. She accessorized the look with some diamond bling, and cut her hair into a super-short pixie that showed off Teyana Taylor's stunning face transformation.