TIFF 2014: Our guide to the best dressed from this year’s red carpet

by Renée Tse September 15, 2014

See our TIFF 2014 best dressed list »

After a whirlwind of red carpet premieres, photo calls and after parties, TIFF 2014 has officially wrapped up for another year. Leaving us starstruck and utterly inspired, we’re certain that 2014 was TIFF’s best year yet (at least in the wardrobe department). With Hollywood’s biggest stars like Jessica Chastain, Reese Witherspoon and Kate Winslet (oh, and a whole bunch of hot dudes) flying into Toronto, you bet we were keeping track of who was wearing what. Whether A-list stars dressed up or dressed down for their events, they did it right. Don’t believe us? We’ve got 56 stunning looks to prove it.

Some stars opted to play it safe on the red carpet in LBDs (looking at you, Jennifer Aniston), but plenty of them showed off their daring personalities in colourful, printed pieces. Kristen Wiig kicked the festival off in a Suno long-sleeved dress and Amanda Seyfried reminded us that summer ain’t over just yet in a Valentino laced frock. But Elizabeth Banks totally got the print look down pat in a blue floral Chloé pantsuit – brownie points for rocking a crop top from American Apparel for the ultimate high-low outfit.

But it wasn’t just the vets who got it right at TIFF. Both Chloe Grace Moretz and Hailee Steinfeld went all out fashion-wise, in looks that rivalled the chicness of legends like Jane Fonda and Julianne Moore. Going from cool to glam with such ease in noteworthy pieces from Dior, Christopher Kane and Dolce & Gabbana, the younger generation is definitely making sure they’re not overlooked.

All that being said, if we had to pick one Queen of TIFF 2014, we can’t think of anyone more deserving than Keira Knightley. Pulling out a total of five best-dressed worthy dresses (not including the looks she rocked at photo calls), we honestly can’t decide which outfit we loved most. While she did surprise us with a few non-Chanel pieces (and then a couple of stellar pieces from her go-to label), we’ve got to say her most recent look by Michael van der Ham may just be one of our fave looks ever. Even Brit It girl Cara Delevingne, who debuted in true model form, couldn’t sway us from our decision. All hail Keira!

Photography by Giordano Ciampini

Photography courtesy of Holt Renfrew

Photography by Kayla Rocca

Photography by Gio Ciampini

Photography by Tom Sandler

Photography courtesy of Grey Goose Soho House

Photography courtesy of Holt Renfrew

Photography courtesy of Holt Renfrew

Photography courtesy of Holt Renfrew

tiff 2014 best dressed chloe grace moretz

Photography courtesy of Holt Renfrew

Photography by Gio Ciampini

Photography by Kayla Rocca

Photography by Tommaso Boddi/Getty Images

Photography by Gio Ciampini

Photography courtesy of Grey Goose Soho House

Photography by George Pimentel

Photography by Alberto E. Rodriguez/Getty Images for LTLA

Photography courtesy of Grey Goose Soho House

Photography courtesy of Grey Goose Soho House

Photography courtesy of Holt Renfrew

Photography by Jason Merritt/Getty Images

tiff 2014 best dressed charlotte gainsbourg

Photography by Ernesto Di Stefano/WireImage

Photography by Kayla Rocca

Photography by Kayla Rocca

Photography by Kayla Rocca

Photography by Alberto E. Rodriguez/Getty Images

Photography by Gio Ciampini

Photography by George Pimentel

Photography courtesy of Grey Goose Soho House

Photography courtesy of Miu Miu

tiff 2014 best dressed reese witherspoon

Photography by George Pimentel

Photography courtesy of Holt Renfrew

Photography courtesy of Holt Renfrew

Photography courtesy of Holt Renfrew

Photography courtesy of Holt Renfrew

Photography by Gio Ciampini

Photography by Jason Merritt/Getty Images

Photography by Gio Ciampini

Photography by Jason Merritt/Getty Images

Photography by Sonia Recchia/ Getty Images for Grey Goose Vodka

Photography courtesy of Grey Goose Soho House

Photography by Gio Ciampini

Photography by George Pimentel/Getty Images

Photography by Sonia Recchia/Getty Images for GREY GOOSE Vodka

Photography by Gio Ciampini

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tiff 2014 best dressed Greta-Gerwig

September 4, 2014: Greta Gerwig in Balenciaga at the premiere of The Humbling.

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tiff 2014 best dressed rene russo

September 5, 2014: Rene Russo at the Variety Studio event at Holt Renfrew.

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tiff 2014 best dressed kristen wiig

September 5, 2014: Kristen Wiig in Suno on the Welcome To Me red carpet

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tiff 2014 best dressed naomi watts

September 5, 2014: Naomi Watts in Stella McCartney at the St. Vincent premiere.

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tiff 2014 best dressed diane keaton

September 5, 2014: Morgan Freeman and Diane Keaton at the Ruth and Alex premiere

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tiff 2014 best dressed rene russo

September 5, 2014: Rene Russo at the Soho House presented by Grey Goose

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tiff 2014 best dressed salma hayek

September 6, 2014: Salma Hayek at the Variety Studio in Holt Renfrew.

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tiff 2014 best dressed jennifer garner

September 6, 2014: Jennifer Garner at the Variety Studio in Holt Renfrew.

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tiff 2014 best dressed cara delevingne

September 6, 2014: Cara Delevingne at the Variety Studio in Holt Renfrew.

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tiff 2014 best dressed chloe grace moretz

September 6, 2014: Chloe Grace Moretz in Sonia Rykiel and Saint Laurent at the Variety Studio in Holt Renfrew.

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tiff 2014 best dressed rosario dawson

September 6, 2014: Rosario Dawson dressed in Fall 2014’s hottest colours on the Top Five red carpet.

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tiff 2014 best dressed janet gretsky

September 6, 2014: Wayne Gretzy and Janet Jones Gretzky at the premiere of The Sound and the Fury.

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tiff 2014 best dressed jennifer garner

September 6, 2014: Jennifer Garner in Stella McCartney at the Men, Women and Children premiere

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tiff 2014 best dressed kate beckinsale

September 6, 2014: Kate Beckinsale in Azzaro Couture for The Face Of An Angel premiere.

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tiff 2014 best dressed cara delevingne

September 6, 2014: Cara Delevingne made us green with envy on the The Face Of An Angel red carpet

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tiff 2014 best dressed amanda seyfried

September 6, 2014: Amanda Seyfried in Valentino at the premiere of While We’re Young.

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tiff 2014 best dressed naomi watts

September 6, 2014: Naomi Watts in Antonio Berardi at the While We’re Young world premiere.

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tiff 2014 best dressed salma hayek

September 6, 2014: Salma Hayek at the Soho House hosted by Grey Goose

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tiff 2014 best dressed cara delevingne

September 6, 2014: Cara Delevingne at The Face of an Angel after party at the Soho House

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tiff 2014 best dressed kate beckinsale

September 6, 2014: Kate Beckinsale in Alice + Olivia at The Face of an Angel after party at the Soho House

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tiff 2014 best dressed jessica chastain

September 6, 2014: Jessica Chastain in Giorgio Armani at the designer label’s TIFF party.

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tiff 2014 best dressed octavia spencer

September 6, 2014: Octavia Spencer Tadashi Shojiat the Black and White after party.

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tiff 2014 best dressed greta gerwig

September 6, 2014: Greta Gerwig stood out in a metallic multicoloured dress at the Soho House.

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tiff 2014 best dressed felicity jones

September 6, 2014: Felicity Jones in Armani Privé at the Soho House hosted by Grey Goose

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tiff 2014 best dressed jessica chastain

September 7, 2014: Jessica Chastain in Dior at the Variety Studio in Holt Renfrew.

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tiff 2014 best dressed haley-bennett

September 7, 2014: Haley Bennett in Ulyana Sergeenko at the The Equalizer premiere

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tiff 2014 best dressed chloe grace moretz

September 7, 2014: Chloe Grace Moretz in Dior at the The Equalizer premiere

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tiff 2014 best dressed charlotte gainsbourg

September 8, 2014: Charlotte Gainsbourg in Louis Vuitton on the Samba red carpet

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tiff 2014 best dressed tina-fey

September 7, 2014: Tina Fey in Christian Siriano This Is Where I Leave You premiere.

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tiff 2014 best dressed abigail spencer

September 7, 2014: Abigail Spencer in Dolce & Gabbana This Is Where I Leave You premiere.

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tiff 2014 best dressed jane-fonda

September 7, 2014: Jane Fonda at the This Is Where I Leave You premiere

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tiff 2014 best dressed anna kendrick

September 8, 2014: Anna Kendrick In Kaufmanfranco at The Last Five Years premiere.

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tiff 2014 best dressed amanda seyfried

September 8, 2014: Amanda Seyfried in Mary Katrantzou at the Tusk premiere.

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tiff 2014 best dressed jena malone

September 8, 2014: Jena Malone in Emilio Pucci at the premiere of Time Out of Mind.

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tiff 2014 best dressed felicity jones

September 8, 2014: Felicity Jones in a Balenciaga at The Theory for Everything post-screening party.

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tiff 2014 best dressed elizabeth banks

September 8, 2014: Elizabeth Banks in Chloé at the Love & Mercy after-party at the Soho House.

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tiff 2014 best dressed keira knightley

September 8, 2014: Keira Knightley in Miu Miu at the HFPA & InStyle’s 2014 TIFF Celebration.

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tiff 2014 best dressed reese witherspoon

September 8, 2014: Reese Witherspoon in Dolce & Gabbana at the post-screening party of The Good Lie.

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tiff 2014 best dressed felicity jones

September 8, 2014: Felicity Jones in Christian Dior at the Variety Studio Event by Holt Renfrew

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tiff 2014 best dressed keira knightley

September 8, 2014: Keira Knightley in Chanel at the Variety Studio event by Holt Renfrew

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tiff 2014 best dressed rose byrne

September 8, 2014: Rose Byrne looked business casual at the Variety Studio event by Holt Renfrew

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tiff 2014 best dressed hailee-steinfeld

September 8, 2014: Hailee Steinfeld in Christopher Kane at the Variety Studio Event by Holt Renfrew

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tiff 2014 best dressed kate bosworth

September 8, 2014: Kate Bosworth in Emilio Pucci at the Variety Studio event by Holt Renfrew

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tiff 2014 best dressed julianne moore

September 8, 2014: Julianne Moore in Chanel at the Still Alice premiere

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tiff 2014 best dressed rose byrne

September 8, 2014: Rose Byrne in 3.1 Phillip Lim at the Adult Beginners premiere

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tiff 2014 best dressed jennifer aniston

September 8, 2014: Jennifer Aniston in a Valentino top and Emanuel Ungaro skirt the Cake premiere

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tiff 2014 best dressed anna kendrick

September 8, 2014: Anna Kendrick in J. Mendel at the Cake premiere

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tiff 2014 best dressed reese witherspoon

September 8, 2014: Reese Witherspoon in Saint Laurent at the Wild premiere

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tiff 2014 best dressed kate bosworth

September 8, 2014: Kate Bosworth in Hugo Boss at the Still Alice after party

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tiff 2014 best dressed julianne moore

September 8, 2014: Julianne Moore in Tom Ford at the Still Alice after party

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tiff 2014 best dressed hailee-steinfeld-2

September 8, 2014: Hailee Steinfeld in Dolce & Gabbana at the The Keeping Room after party

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tiff 2014 best dressed keira knightley

September 9, 2014: Keira Knightley at The Imitation Game after party

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tiff 2014 best dressed sarah gadon

September 9, 2014: Sarah Gadon in Antonio Marras at the Maps to the Stars premiere

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tiff 2014 best dressed keira knightley

September 10, 2014: Keira Knightley in Michael van der Ham at the Laggies premiere.

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tiff 2014 best dressed anna kendrick

September 11, 2014: Anna Kendrick in Miu Miu at The Voice after party hosted by Grey Goose and Remstar Films

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tiff 2014 best dressed kate winslet

September 14, 2014: Kate Winslet in a green and black floor-length gown on the A Little Chaos red carpet.

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