One year ago, Da'Vine Joy Randolph was on a dual award season and red carpet style hot streak. Every show delivered her best dress yet—plus a shiny new Golden Globe, Critics' Choice, and SAG Award statue to go with it. It all culminated in her Best Supporting Actress Oscar win for The Holdovers, accepted as she sparkled in a custom, powder blue Louis Vuitton gown with feathered sleeves and a flowing chiffon train. She'd played a part that made award season history. She looked the part of a timeless star when she accepted her trophy.
Cut to the 2025 Oscars, where Da'Vine Joy Randolph would deliver one of the evening's best red carpet fashion moments in dress symbolizing just how far she's come. Returning to the ceremony as a presenter for the category she won the previous year, the star dressed to showcase the expressive freedom she's found after dominating the Academy Awards campaign trail.
"Last year's clear intention was kind of like reinventing Old Hollywood glam," she tells me over the phone en route to the red carpet. Classic shapes and silhouettes selected by styling duo Wayman + Micah had helped her convey award-worthy energy, all topped with leading-lady golden blonde hair. This year, she's expanding her horizons. "What's been fun this year just in general, but especially for tonight, is allowing me to be a little more, I don't know, edgy or risqué."
"I don't know what the right word is," she laughs, but she can describe the feeling. After taking the formal, Serious Actress route with sculptural, one-shoulder gowns that manifest a best possible awards outcome—she likens it to the way musicians like Sabrina Carpenter or Taylor Swift campaigned for Grammys with album-themed outfits—Randolph feels like she can finally let loose. "Now it's fun to kind of let your hair down, so to speak, you know what I mean? I don't have to be so pageant-y."
In her sweep of the recent Paris couture runways, Randolph and her team found a designer who could still deliver on the elegant, timeless aura the Oscars asks for while also allowing her to "have just a bit more freedom, to try some new things out and experiment." Tamara Ralph, whose gowns have also graced the likes of Jennifer Lopez, Florence Pugh, and fellow Oscars presenter Halle Berry, "really impressed" the actress.
She was thrilled when Ralph signed on to created her 2025 Oscars dress, and even more overcome with the final result: a beaded, corseted black gown set with a satin rosette, from which tiers of coordinating fabric draped around her waist and extended into a flowing skirt.
"I have to say of the things that I've seen from her, I've never seen her make anything like this before, with beadwork and yards and yards of fabric," Randolph says. "There's a lot of drama. There's a dramatic train, there's a chiffon scarf that drags behind me."
Even the color felt like a change of pace after last year's Oscar-winning pastel. "We went with black, which I don't think I ever would have done."
The experimentation didn't end with her dress's shape and palette. Hair stylist Tai Simon and makeup artist Sheika Daley helped Randolph embrace an entire new beauty look for the night. A warm ginger pixie cut and micro bangs replaced last year's blonde waves, complemented by a neutral lip and bold lashes.
“We love to experiment and play with color, so for tonight, we of course, went with a gorgeous cowboy copper by Danger Jones Gloss Tones," Tai Simon, her hairstylist, says. "The sleek and sultry cult and color modernizes the classic starlet look of Da’Vine’s gorgeous jeweled gown.”
And, it showed Randolph's beauty range. "We tried different things and decided, let's play. Let's give them another option, another opportunity to see a different side of me," she says, "which that's why I love fashion and beauty so much. It gives you an opportunity to recreate yourself, evolve yourself, and be playful."
[T]hat's why I love fashion and beauty so much. It gives you an opportunity to recreate yourself, evolve yourself, and be playful.
Randolph's biggest constants from her year as a nominee to her return to present have been the people around her. First, there's the core group who has prepared her for every red carpet and award ceremony where she's been in the spotlight. "At this point we've worked with each other so long, we just move so fluidly with one another. It's always great vibes," Randolph says. "It's like having girlfriends over to just shoot the shit." And when all the carpet-hopping and travel wears on her energy, she trusts them to handle her glam while she dozes off in the makeup chair.
Then, there are the fellow actors—nominees last year, presenters this year—she's bonded with on every step of the grueling campaign trail. "What was so beautiful about this year is to see that that bond still exists and that people really have an understanding and empathy for what we go through," she says. "It's exciting, but it's a huge commitment."
Da'Vine Joy Randolph's night with her team only started with her Tamara Ralph gown. A few hours later, after she handed this year's Best Supporting Actress trophy to Zoe Saldaña, they'd meet again to change the actress into a trophy-hued, off-the-shoulder gown for the Oscars after-party; she'd also conceal her micro bangs beneath auburn, Ariel-esque waves.
Even if outfit changes and bold beauty adjustments weren't practically written into the Oscars night dress code, this star would be able to justify switching up her look mid-evening.
"I think whether you're an Oscar winner, nominee, whatever it is, even the everyday woman, I think you should do as much as you can to be your best self," she says. That philosophy includes showing the spectrum of your style in a single night.
Photographer Conrad Khalil | Stylist Wayman + Micah | Hair Stylist Tai Simon | Makeup Artist Sheika Daley
