Mikey Madison Has Had A Head-Turning Style Transformation

Mikey Madison was catapulted into stardom with her nuanced performance in “Anora,” taking home a Best Actress Oscar for her portrayal of the titular Brooklyn sex worker. While the rising star has seen major success within her short-lived career, she’s also undergone a head-turning style transformation since breaking into the industry as a teen. “I started working with [stylist] Jamie Mizrahi, who I really like and I think really understands my sense of style, which has evolved quite a bit over the past two years,” she told Vogue in 2024.

Though she appeared in a few projects beforehand, Madison’s breakout role was on the 2016 series “Better Things,” with the California native starring alongside Pamela Adlon, Hannah Riley, and Olivia Edward for five seasons. She went on to appear in major films like Quentin Tarantino’s “Once Upon a Time in Hollywood” and the horror reboot “Scream,” starring goth glam queen Jenna Ortega, before landing her Oscar-winning role. While her fashion identity has definitely evolved as her career has grown, Madison’s sense of style has continually wowed us over the years.

Mikey Madison’s earliest red carpet appearances coincided with the 2016 debut of “Better Things,” with the budding actor stepping out for the season premiere of fellow FX series “You’re The Worst” in late August. The California native opted for a floral-patterned maxi dress for the event, with the For  Love & Lemons piece featuring a V-shaped neckline, puffed sleeves, and a centered skirt slit. She paired the red-and-orange dress with strappy brown heels and silver rings. As for beauty, the actor wore her hair in a side braid with face-framing pieces and opted for a shimmery but subtle gold eyeshadow.

This era of Madison’s journey marks both her budding style identity and her firm entry into the industry. While she’s spoken about her long-running interest in fashion, she’s also opened up about the impact that “Better Things” had on her as a person and an actor. “I literally was a girl when I started and then I left the show a woman, and so I grew up in such a big way,” she told GQ. “I learned how to be an actor. I learned about work ethic, a little bit about emotional preparation. I learned how to play a character that feels different from who you are.”

Fans of “Anora” know that Mikey Madison’s fashion leading up to her big Oscar win in 2025 channeled the glamor of vintage Hollywood, with the actor telling InStyle that “film stars of the ’50s, ’60s and ’70s” are her style inspiration. “I think I really romanticize those eras of cinema and of course the leading ladies too!” she said. In this way, it’s not surprising that some of the star’s earlier fashion hints at her love of classic style icons.

At the 2018 FX All-Star Party, Madison wore a deep red dress featuring a deep-V halter top and a pleated, midi-length skirt. The silhouette is very reminiscent of the ’50s dresses worn by stars like Marilyn Monroe, while the rich color also gives the ensemble a vibe of allure and mystique. The actor opted for simple styling for the outfit, accessorizing with matte black heels and wearing her long hair around her shoulders with face-framing waves. We love this stunning 2018 look, but it’s just a glimpse of the glamor to come from the rising star.

After appearing in “Once Upon a Time in Hollywood,” playing an unhinged Marilyn Manson follower, Mikey Madison attended the 2020 Vanity Fair Oscar Party in a head-turning gold dress and luxury jewelry. While her smaller part in the star-studded Tarantino film led to her award-winning role in “Anora” — with director Sean Baker approaching the young star after seeing her in “Once Upon a Time in Hollywood” and “Scream” — Madison’s fashion during this era of her career demonstrated that the California native isn’t afraid to make a statement with her wardrobe.

The star wore a Fannie Schiavoni gown with an asymmetrical hemline and a strappy, V-shaped neckline to the afterparty. She paired the piece with a statement Paula Mendoza necklace and matching gold heels, opting for a subtle smoky eye and nude lip color. As Pinterest predicted 2025 would be all about the goddess complex, it seems that Madison was both head-turning and ahead of the times with this liquid gold look.

Playing a Brooklyn sex worker, Mikey Madison underwent a major transformation for her “Anora” role, learning to pole dance, shadowing women in the industry, and collaborating on wardrobe and beauty to bring a realness to the character. “When I put on Ani’s heels and tight dresses, and I have my hair and makeup done, I walk differently,” she told Backstage. “Ani’s long nails make me move my hands in a different way. I have all this attitude on the tips of my fingers.”

While Madison had a very specific beauty transformation for “Anora,” the actor hasn’t shied away from more risqué fashion in her personal life. An example of this is the floor-length gown she wore to the Season 5 celebration of “Better Things” in 2022, with the black dress featuring a belly-button-revealing neckline. The actor added silver accents to the outfit, posing in silver-tipped heels and sporting a sparkly NUÉ handbag. Though playing Ani brought Madison a newfound sense of sensuality, risqué elements have long been present in her wardrobe.

For the 2025 award show season, Mikey Madison took fashion inspiration from the glamor and luxury of Old Hollywood. While her Hepburn-inspired Academy Awards gown unfortunately landed the star on our 2025 list of worst-dressed Oscar attendees, she’s managed to turn heads with stunning looks at other events. For example, Madison served simple elegance at the BAFTA Film Awards in February, wearing a custom column-shaped gown with a matching shawl. “Tonight, I’m wearing a queen-colored Prada dress,” she told British Vogue in a behind-the-scenes video. “It’s long, strapless, and there’s a shawl. It’s really beautiful and classic.”

The actor accessorized with an archival Tiffany necklace “made up of these little diamond bows,” with the piece being part of her look’s vintage influence. “The history of Tiffany is so romantic, and one of my favorite films is ‘Breakfast at Tiffany’s,'” she explained. “I always think of Audrey Hepburn when I wear Tiffany, so I’m excited.” The entire ensemble was elegant and classic — words that aptly describe Madison’s early 2025 fashion era. As her career-spanning transformation shows that she’s a fashion icon to watch, we can’t wait to see what comes next for the Oscar-winning star.