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The best red carpet looks from day five of TIFF, featuring Justin Timberlake and Michelle Williams

By Jean Grant| Photography by George Pimentel
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Tuesday was full of mega-watt celebs making questionable fashion choices: Matt Damon and Kurt Russell walked the red carpet in slouchy jeans, Mark Wahlberg sported a seriously ill-fitting suit and Kate Hudson decided to channel her inner ‘80s Madonna. Thankfully, there were still a few moments of sartorial glory, courtesy of a stunner from Michelle Williams and a few cocktail party–appropriate frocks from Tatiana Maslany and Suki Waterhouse. Here, our favourite looks from day five of the festival:

Michelle Williams upstaged all her co-stars in a dazzling Louis Vuitton gown at the premiere of her film Manchester by the Sea:

The best red carpet looks from day five of TIFF, featuring Justin Timberlake and Michelle Williams

Justin Timberlake, whose concert documentary Justin Timberlake and the Tennessee Kids also premiered yesterday, added some 1970s pizzaz to a plaid suit with paisley tie and leather ankle boots:

The best red carpet looks from day five of TIFF, featuring Justin Timberlake and Michelle Williams

At the screening of the thriller Deep Water Horizon, star Gina Rodriguez floated down the red carpet in a dreamy Badgley Mischka dress.

The best red carpet looks from day five of TIFF, featuring Justin Timberlake and Michelle Williams

Score one for the home team: Tie Domi’s polished look beat out Mark Wahlberg‘s oversized suit:

The best red carpet looks from day five of TIFF, featuring Justin Timberlake and Michelle Williams

Suki Waterhouse wore a sorta-affordable dress by Self Portrait to the premiere of The Bad Batch (her co-star Jason Momoa donned a more...interesting look):

Orphan Black star Tatiana Maslany stepped out in a chic dress by designer Johnathan Simkhai (the FLOTUS is also a fan, and it can be yours for just over $900):

Nigerian actress Somkele Iyamah-Idhalama, star of drama The Arbitration, wore a super-cool striped ensemble by Lagos-based brand Meena:

Jean Grant has been a freelance writer since 2015, covering a range of lifestyle topics like shopping, interiors, wellness and culture for publications like Maclean’s and Toronto Life. She also enjoys working with brands to develop custom content, and shares personal essays through her Substack newsletter, Nobody is Thinking About You.
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