TIFF 2024: The best, worst and most bizarre red carpet looks of all-time from the Toronto International Film Festival

The 2024 Toronto International Film Festival is here — and so are some of the biggest names in Hollywood. The world-renowned film festival kicks off Thursday and runs through Sept. 15. This year's lineup is stacked with buzz-worthy films, including Frances Ford Coppola's Megalopolis, starring Adam Driver, and Nicole Kidman's erotic thriller Babygirl. Other notable premieres include Demi Moore's horror film The Substance, Zoe Saldaña and Selena Gomez's dramatic musical Emilia Pérez and the world premiere of Nightbitch, a dark comedy starring Amy Adams based on the novel by Rachel Yoder.

Although it may not have the grand staircase of the Cannes Film Festival or dramatic arrivals by boat like the Venice Film Festival, TIFF's red carpets still pack a fashion punch. Ahead of this year's festivities, we've gathered some of the best —and worst — red carpet moments from TIFF.

Keep reading to see some unforgettable (and sometimes regrettable) looks.

BEST: Taylor Swift

Swift hit the red carpet for a special "In Conversation With... Taylor Swift" at TIFF in 2022. The appearance celebrated the release of her short film All Too Well: The Short Film set to the 10-minute version of her opus by the same name. Swift shimmered in a gold grecian-inspired Louis Vuitton gown that remains one of her best red carpet looks to date.

WORST: Lady Gaga

Lady Gaga is known to take big risks with her career — and fashion. Although there are plenty of moments where Gaga's risk-taking pays off, there are a slew of fashion moments that miss the mark completely. Case in point: Her ill-fitting Lanotta Studios look at TIFF in 2017 for the premiere of her documentary Gaga: Five Foot Two. The bizarre ensemble looked as though it was made for someone 6 ft 2" — and given to Gaga in a pinch.

BEST: Kate Hudson

Hudson was the epitome of red carpet glamour at the world premiere of Glass Onion: A Knives Out Mystery at TIFF in 2022. Hudson's strapless Carolina Herrera dress with floral embellishment and matching red lip were one of the stand-out looks from the festival —and one of her most daring red carpet looks ever.

WORST: Anne Hathaway

Rodarte and Anne Hathway rarely make mistakes, but the two were a recipe for disaster at the 2016 TIFF premiere of her film, Colossal. From head-to-toe, this look is probably one Hathaway would like us to forget. Unfortunately for Annie, this half-up, half-down hairstyle and embellished lace mini-dress is seared in the back of our minds like an unspeakable trauma. When you know better, you do better — and Hathaway has done much, much better since then.

BEST: Jessica Chastain

Jessica Chastain is TIFF. The Oscar-winning actress is a staple at the Canadian film festival and delivers unforgettable fashion moments, like this Armani Privé gown at the premiere of her film, Memory, in 2023. Chastain's plunging column gown featured triangle embellishments that added a pop of colour to the otherwise classic black ensemble. The star paired the look with a serpentine diamond necklace and sleek red tresses for a glamorous look with just the right amount of edge.

WORST: Drew Barrymore

Roller girls have edge — and Drew Barrymore definitely went method to promote her film Whip It at TIFF in 2009. Long before her talk show days, Barrymore served as actor, producer and director of the roller derby film starring Elliot Page and Kristen Wiig. Although such a feat is cause for celebration, Barrymore's quirky ensembles and dip-dyed hair were drawing attention for all the wrong reasons.

BEST: Jennifer Aniston

She might be known for great hair and a penchant for black dresses, but Jennifer Aniston went for something more colourful at the 2013 Toronto International Film Festival. The actress stepped out in a show-stopping French blue Vivienne Westwood look for the premiere of her indie film, Life of Crime, co-starring Isla Fisher and Will Forte.

WORST: Nicole Kidman

Nicole Kidman is red carpet royalty — but even Oscar winners have off days. In 2017, Kidman celebrated the premiere of her film The Killing of a Sacred Deer in a colourful Valentino look that featured multiple patterns and a high neckline. The high fashion look didn't quite translate to the red carpet, and made for an overwhelming cluster of patterns.

BEST: Ava DuVernay

Ava DuVernay's yellow Miu Miu dress was a bright spot on the 2023 TIFF red carpet. Although a writers' and actors' strike loomed over the annual festival, DuVernay's look was a ray of light as she celebrated the premiere of her film, Origin.

WORST: Brie Larson

In 2015, all eyes at the TIFF were on Brie Larson, who was generating Oscar buzz for her performance in Room. Larson's red carpet looks, however, were also garnering attention — just not for the right reasons. Although her asymmetrical royal blue look isn't terrible, the faux-hawk pushes this look over the edge to unsalvageable.

BEST: Gabrielle Union

Gabrielle Union's Vivienne Westwood gown and statement choker featuring the designer's emblem was the perfect choice for the premiere of her film The Incident at TIFF in 2022. The thigh-high slit of Westwood's signature silhouette added a bit of spice to the otherwise classic silk gown.

WORST: Emma Corrin

Emma Corrin's style has always been avant garde, but they took things to the next level at the 2019 TIFF premiere of My Policeman. Corrin's sheer Miu Miu bodysuit with comically long sleeves seemed out of place on the film's red carpet. Points for creativity, but some runway looks don't always translate to the red carpet.

BEST: Natalie Portman

Portman is no stranger the TIFF red carpet, but in 2015 the star was on-hand to celebrate the premiere of her directorial debut, A Tale of Love and Darkness. Portman dressed for the occasion in an asymmetrical nude-coloured gown with star detail by Dior. Her magenta lip and sleek hairstyle were the perfect pairing for the occasion, which affirmed that Portman is so much more than a leading lady.

WORST: Kate Beckinsale

Kate Beckinsale is not someone who likes to play it safe on the red carpet. In 2022, the star arrived for the TIFF premiere of her film The Prisoner's Daughter in a structural Bach Mai dress that could have been a stunning red carpet moment — if only she didn't opt for the bizarre fingerless latex gloves.

BEST: Timothée Chalamet

Long before he was starring in blockbusters like Dune, Timothée Chalemet was an indie film darling and a fixture on the festival circuit. In 2018, fresh off the success of Call Me By Your Name, Chalamet returned to TIFF to celebrate his film, Beautiful Boy, co-starring Steve Carrell. This time, Chalamet hit the red carpet in a floral Haider Ackermann suit that signalled his status as a bonafide movie star.

WORST: Emma Stone

Emma Stone may be a two-time Oscar winner, but back in 2010 she was a red carpet neophyte looking to find her signature style. Stone hit the red carpet of the TIFF premiere of her film Easy A in a one-shoulder mini-dress with a '60s bouffant style hairdo that didn't quite hit the fashion mark. Luckily, the Stone is now a Louis Vuitton ambassador and privy to their latest fashions, so looks like this can remain firmly in the past.

BEST: Jane Fonda

Jane Fonda hit the red carpet for the premiere of her film This Is Where I Leave You in a black jumpsuit by Hanley that featured chiffon sleeves. The look was a polished alternative to the usual red carpet fare of gowns and suits and was perfect for Fonda, who later posed in a deep lunge on the red carpet.

WORST: Riley Keough

Long before she played the lead of Daisy Jones and The Six, Keough showed off her flare for bohemian fashions in a pink satin and lace mini-dress by Louis Vuitton at the 2018 TIFF premiere of Hold The Dark. Although it's clear that the look was going for "easy, breezy, beautiful" it looked closer to sleepwear than red carpet-worthy attire.

BEST: Michelle Monaghan

Michelle Monaghan hit a sartorial high note at the 2022 TIFF premiere of her film, Nanny. The actress's chainmail-inspired Christopher Esber gown with leather detailing was a red carpet standout and one of our favourite looks in TIFF history.

WORST: Jessie Buckley

Jessie Buckley's Erdem gown at the 2022 TIFF premiere of Women Talking looked right out of a period film. The ruffles, neckline and long sleeves were fabric overkill — and not necessarily suitable for final legs of Canadian summer.

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