Rita Moreno's Stunning Academy Awards Dresses, Ranked By Timelessness

Rita Moreno, the EGOT-winner best known for her Oscar-winning performance in "West Side Story," has had a long, fruitful acting career. Naturally, that translates to a lot of red carpet looks over the past eight decades. From the smoldering, sultry looks she wore during her younger years to the quirky, elegant styles she's rocked as she's aged, Moreno knows how to own the red carpet.

First and foremost, the star doesn't believe in letting other people dictate how to dress. While she thinks some of her sexier looks may have contributed to the way she was objectified during her early career, she doesn't regret dressing for herself. "You can dress any damn way you please," she told People. "You can wear as many loop earrings and as low-cut a neck as you want."

But after all these years, Moreno still stuns us with her red carpet looks. That's in part because she doesn't dress for trend cycles — she dresses for personal expression, and her outfits almost always include a playful, personal element. Personal style is timeless, which is why it's worth finding your own. Moreno doesn't kowtow to ageism. Instead, she rocks bold look after bold look, even into her later years. "I love that her style has stayed fun and a little quirky throughout her career!" wrote one Reddit user. "She's a true icon." But while her red carpet looks have consistently been chic, the star has worn some looks that were more timeless than others.

For the 2018 Academy Awards, Rita Moreno wore a reworked version of her 1962 Academy Awards dress, modifying the formerly high neckline into a strapless bodice. "This is the dress. It's been hanging in my closet, and I go and stroke it now and then," she said on the red carpet, via People. Clearly, the look is among Moreno's favorites, and its reappearance is proof of its timelessness. Still, this modernized version ranks lowest because it's less balanced than its high-neck iteration. In fact, updating the design detracted from its timelessness.

Rita Moreno looked incredibly elegant in the burgundy gown that she wore for the 2021 Academy Awards. The strapless number had a mermaid skirt, which the star paired with a coordinated chenille jacket and chunky beaded necklace. With this look, Moreno proved that she's among the Hollywood celebrities confronting aging with confidence, since she didn't shy away from a bold fashion statement on the red carpet. This look is pretty timeless, but it ranks slightly lower since the strapless dress and oversized beads are tied to 2016 and 2026 trends.

Rita Moreno showed up to the 2024 Academy Awards in a sculptural black velvet Badgley Mischka gown and completely stole the show. "It's a privilege to have our designs adorn such an iconic figure," the brand wrote beneath an Instagram snap of Moreno wearing the gown. The striking, avant-garde design completely transcends trend cycles, and Moreno rocked the striking gown with a fresh pixie cut — a perfect hairstyle for older women who want to stay youthful. "We should all be so lucky to look this fab in our 90s!!!" wrote one Reddit user.

To accept her 1962 Oscar for Best Supporting Actress in "West Side Story", Rita Moreno wore a high-necked black gown with a stunning printed skirt. This was one of Moreno's favorites as well, since she wore a modified version of it in 2018, which ranked #5 on this list. While the print and shape of this dress clearly reflect the fashion trends of the '60s, its sophisticated neckline still looks just as good from the vantage point of the 2020s, and the ballgown shape would fit in on a red carpet today.

At the 2022 Academy Awards, Rita Moreno donned a sculptural black Carolina Herrera dress and a unique feathered hat. Despite the all-black palette, the look stood out thanks to its avant-garde silhouette and the contrasting textures. With this look, Moreno proves that the best way to look timeless is to focus on honing personal style, because it's way less subject to the ebbs and flows of time. "I just thought, What the hell?" said Moreno of the playful statement look, via People. "And I just love it the way I look in it."

To determine the relative timelessness of each look, we considered a range of factors, including silhouette, print, and fabric choices. Gowns that could be easily assigned to a particular decade were ranked lower than those that were less readily identifiable, with looks that weren't from any obvious era appearing more timeless. However, consideration was also given to the overall success of the look, with gorgeous trendier looks still holding rank if they could reasonably exist on the red carpet during any time period.