Maisy Stella’s Critics Choice Dress Delivers Timeless Glamour

“It’s a crazy feeling waking up this morning to messages and texts. … It is real! It actually happened!” Maisy Stella tells Who What Wear of her Critics Choice Awards win for Best Young Actor/Actress. Since the coming-of-age comedy My Old Ass first premiered at the 2024 Sundance Film Festival, all eyes have been on Stella in her film debut. Critics are praising the breakout star for her charismatic turn as Elliott, a free-spirited teen who comes face-to-face with her 39-year-old self during a mushroom trip. The win on Friday was an exciting and fitting end to what has been a whirlwind yearlong press run.

For the occasion, Stella—with help from her stylist Tara Swennen—selected a black crêpe gown with cutout and pearl details from Pamella Roland’s Pre-Fall 2025 collection. “The dress was probably my favorite one that I’ve gotten to wear yet,” she says, adding that she was immediately drawn to its unique yet timeless silhouette and floating-pearl accent. For accessories, Stella paired the gown with Effy jewels, a black Kate Spade bag, and black satin Giuseppe Zanotti heels.

The statement look was the latest high note in a press tour marked by a series of black-and-white looks. When it comes to red carpet dressing, Stella says she likes a nice mix of feminine and masculine silhouettes and has a pretty strong gut in knowing which look is best. “If I feel myself in it, then it’s probably the one,” she says.

Taking inspiration from a photo Stella pulled from Pinterest, hairstylist Sylvia Wheeler created a half-up, half-down look that perfectly suited the 21-year-old’s new dark-brown locks and the Old Hollywood feel of the dress. Meanwhile, makeup artist Mélanie Inglessis leaned into a fresh and natural beauty look by prepping Stella’s skin with Embryolisse’s Lait-Crème Concentré and Radiant Complexion Cream before applying Armani Beauty’s Luminous Silk Foundation in #4. For the eyes, Inglessis used Bobbi Brown’s Cream Eyeshadow Stick in Ruby Shimmer topped with Victoria Beckham Beauty’s Satin Kajal Liner in Cocoa and Estée Lauder’s Turbo Lash. She finished off with Femmue’s Lip Sleeping Mask followed by Le Rouge Français’s Liptick in Wantura and Make Up For Ever’s Artist Color Pencil in Endless Cacao on the lips.

Though Stella was battling some pre-carpet jitters, she tells us the vibes in her getting-ready suite at the Pendry Hotel in West Hollywood were great. Kendrick Lamar’s Damn album and “Girls” by The Dare—a favorite pump-up song for Stella—played on Wheeler’s portable speaker as she noshed on some room-service bites.

When Stella arrived on the carpet with her sister Lennon by her side, it was a surreal experience. Here she was at a show she had watched on TV for so long. “It was such an insane room of talent,” she says. “I saw Margaret Qualley and almost died.”

To celebrate her well-deserved win, Stella, Lennon, and friends went to Pace in Laurel Canyon for dinner and a bar afterward. “It was actually so sweet, and I felt so much love. It was a perfect night,” she says.