Before Fashion Month finally kicks off in New York City on September 11, there’s one more major red carpet event to take in: the Toronto International Film Festival. Some years, Toronto gets overlooked between the glitzy boat rides of the Venice Film Festival, the textbook memorable outfits at the MTV VMAs, and all the A-list sightings in the front rows from NYC to Paris. But this year, I’ve found the Toronto International Film Festival’s best-dressed stars to have some of the most noteworthy interpretations of the very same designers fashion people will be discussing in a few days’ time.
In Venice, labels including Dior, Chanel, and Versace soft-launched their incoming creative directors’ new visions—and new ambassadors. Some of that same thread was picked up across the Atlantic, as Anya Taylor-Joy arrived in her own custom Dior moment by Jonathan Anderson and at least two names tried on Alessandro Michele’s new-ish Valentino for size. I’ve also noticed an uptick in labels from the halls of London Fashion Week (like Erdem, chosen by Sydney Sweeney) and some copy-pastes from Paris staples (like Saint Laurent, picked by Tessa Thompson).
So far, the best-dressed stars at the Toronto International Film Festival are celebrating their upcoming projects in names that everyone will be talking about this month. I can think of no better warm-up for the international runway circuit than this refresher on luxury’s favorite clients and their red carpet staples.
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Anya Taylor-Joy wearing Dior
Anya Taylor-Joy attended the 2025 Toronto Film Festival in custom Dior.
(Image credit: Getty Images)
Anyone worried that Anya Taylor-Joy’s streak as a Dior muse would end with a new creative director can rest easy now. The star arrived at the 2025 Toronto International Film Festival in a custom look by Jonathan Anderson that picked up where his debuts in Venice left off. A quintessentially Dior shade of baby blue transformed from an elegant sheath shape up top to a skirt extending away from Taylor-Joy’s body, composed of several interwoven ribbons. As one of the potentially final glimpses at Anderson’s womenswear before his runway debut in Paris, it was a gift to behold.
Maude Apatow wearing Valentino
Maude Apatow made her Toronto International Film Festival debut in Valentino.
(Image credit: Getty Images)
Maude Apatow’s first Toronto International Film Festival as a director was always going to feel special. But for the premiere of Poetic License, she and stylist Mimi Cuttrell decided on an agenda-setting look by Alessandro Michele’s Valentino. The cheery pink satin and feather-dusted cape said the rising star can have her serious career milestone and have fun, too.
Tessa Thompson wearing Saint Laurent
Tessa Thompson attends a Toronto International Film Festival party in Saint Laurent.
(Image credit: Getty Images)
I had a hard time choosing my favorite of Tessa Thompson’s Toronto International Film Festival looks. A runway Chanel strapless dress—complete with pockets—definitely surprised me with its elegant practicality. But I ultimately had to choose the actress’s funnel-neck mini from Saint Laurent’s Fall 2025 runway. Stylist Karla Welch delivered an off-the-catwalk moment to remember, between the rich shade of red, the sharp-as-knives heels, and the nod to one of Paris Fashion Week’s most anticipated collections.
Elizabeth Olsen wearing Emilia Wickstead
Elizabeth Olsen attends the 2025 Toronto International Film Festival wearing Emilia Wickstead.
(Image credit: Getty Images)
There’s more to Elizabeth Olsen’s Emilia Wickstead Fall 2025 gown than meets the eye. The London Fashion Week standout’s sequin-coated gown has slightly off-kilter shoulders and an entirely open back—which Olsen made sure to emphasize on the step-and-repeat. This is the sort of black dress that’s understated, but still eye-catching with its all-over sequins.
Angelina Jolie wearing Gabriela Hearst
Angelina Jolie attends the Toronto International Film Festival in one of her favorite designers.
(Image credit: Getty Images)
Angelina Jolie and Gabriela Hearst are one of the red carpet’s most enduring duos. The actress kept their spirit of collaboration alive on the 2025 Toronto International Film Festival red carpet, when she styled one of the label’s longline trench coats as a fall dress. A flash of semi-sheer tights and a pointed-toe pump transformed her outerwear from another seasonal layer to a photo-worthy moment.
Nia DaCosta wearing Zimmermann
Nia DaCosta attends the Hedda premiere at the 2025 Toronto International Film Festival.
(Image credit: Getty Images)
The average fashion-phile might think of Zimmermann mostly as a destination for ruffled floral dresses and Katie Holmes-approved trenches. But as Nia DaCosta reminded me at the Toronto International Film Festival premiere of Hedda, the brand is just as skilled at understated boho pieces. Her cream turtleneck dress only needed its billowing, cape-like sleeves to make a statement—and make me excited for Zimmermann’s upcoming runway in Paris.
Shailene Woodley wearing Dolce & Gabbana
Shailene Woodley arrived at her first Toronto International Film Festival premiere in Dolce & Gabbana.
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Shailene Woodley started her fall mini dress streak at the 2025 Venice Film Festival, in a Kallmeyer LBD Zoë Kravitz also owns. She kept the party dressing energy up at the Venice International Film Festival, where stylist Alexandra Imgruth sourced a sparkling Fall 2025 Dolce & Gabbana mini. The dress was styled with a punk-rock bralette and knee-high boots on the runway, but Woodley opted for more work-appropriate pumps—and an opaque liner—for her premiere.
Kirsten Dunst wearing Valentino
Kirsten Dunst attends a Toronto International Film Festival Party in Valentino.
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Valentino’s red carpet sweep continued when Samantha McMillen and Kirsten Dunst sourced this cut-out Resort 2026 gown for the Toronto International Film Festival premiere for Roofman. Delicate Sophie Bille Brahe jewelry perfectly complemented the softness of the gown’s gauzy-like fabric and trains off each arm.
Sydney Sweeney wearing custom Erdem
Sydney Sweeney attended the premiere of Christy in custom Erdem.
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Sydney Sweeney and stylist Molly Dickson contrasted the rough-and-tumble nature of the actress’s boxing biopic, Christy, with a princess-like custom gown by Erdem. Designer Erdem Moralioglu, a reliable favorite on the London Fashion Week calendar, combined Sweeney’s penchant for red carpet corsets with a dramatic draped skirt that cascaded from her left hip. Her film is already generating some Oscars buzz—and this is the sort of dress that can help her campaign for the ultimate leading lady trophy.
