STYLE
09/08/2014 02:00 EDT | Updated 09/08/2014 02:59 EDT

TIFF's Most Underrated Red Carpet Looks (PHOTOS)

Evan Agostini via Getty Images
TORONTO - SEPTEMBER 08: Actresses Reese Witherspoon arrives at the gala presentation of 'Penelope' during the Toronto International Film Festival held at Roy Thompson Hall on September 8, 2006 in Toronto, Canada. (Photo by Evan Agostini/Getty Images)

TIFF 2014 is in full swing, and as such, we already have many opinions on various red carpet looks. But considering we still have just under a week of premiere-appropriate fashion to go, we figured we’d take a walk down memory lane to acknowledge the overlooked red carpets of yore.

Here are 10 of our favourite “overlooked” red carpet outfits.

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Most Underrated TIFF Outfits

1. Kate Hudson, 2000

Remember the days of "Almost Famous"? Before Kate Hudson, the Academy Award-nominated actor, was a household name? (Of course you do.) Unsurprisingly, her style was on-point then, too. Embodying the bohemian aesthetic of her "Almost Famous" character, she donned a floor length satin gown with a sheer overlay at the film’s TIFF 2000 premiere. As if Steve Nicks and her fellow music icons had wrapped Hudson in the essence of ‘70s fashion culture.

2. Claire Danes, 2004

Since "My So-Called Life," Claire Danes’ personal style has been both elegant and interesting. (Which, if we may be so bold, are two descriptions that aren’t usually synonymous.) 2004’s premiere of "Stage Beauty" was no exception, as Danes wore her usual blond layers alongside a simple lace slip dress. See: something that would work just as well today as it did ten years ago, and also: something that would make Angela Chase proud.

3. Maggie Gyllenhaal, 2005

Maggie Gyllenhaal actually doesn’t get nearly enough red carpet credit, so let’s right that wrong. In this sheer, ‘30s-esque midi dress, she capitalized on the flapper (or post-flapper) trend before the 1920s pop culture boom we saw over the last couple years. However, the plunging neckline helped bring her look back into 2005 instead of it seeming like the actress was attending a costume party. (She wasn’t: only the premiere for "Trust the Man.")

4. Reese Witherspoon, 2006

Reese Witherspoon’s style has just gotten better since her days as a teen drama queen (don’t any of you forget "Fear," ever), but this 2006 dress at the premiere of "Penelope" embodied her shift from America’s Sweetheart to bona fide Movie Star.™ In this fitted black slip dress, she took a risk which paid off wonderfully: with the texturing across the bust, the lace embellishments, and the blue and cream contrasts, she looked like a force to be reckoned with. Which she still is, obviously.

5. Joy Bryant, 2006

Let’s keep this one simple: no other human on this planet will ever be able to pull off a turtleneck floor length sweater dress again. Especially not one topped with a gold belt. (And if you try, Joy Bryant gets to ask you to please stop.)

6. Sherri Shepherd, 2009

How was Sherri Shepherd helping set trends at the 2009 premiere of "Precious"? Let us count the ways: a variation of animal print, metallics, and gems. By fearlessly combining three looks that we might have thought twice about amalgamating pre-2010, Shepherd came off as daring, but understated. Why? Because she let the dress do its thing, while toning down the accessories.

7. Gabourey Sidibe, 2009

Then, at that same premiere, Gabourey Sidibe – star of "Precious" – got a jump start on the 2010-present colour du jour: orange. And not only that, she did it via vintage influence. While we all sang the praises of the ‘70s last year and a few seasons before thanks to Marc Jacobs and movies like "American Hustle," Sidibe went disco appropriate on the red carpet with an ankle-length sleeved gown embellished with gold – four years before we saw the same pieces in chain stores.

8. Robin Wright, 2009

In which Robin Wright wears a 1980s-inspired leather mini dress to the premiere of "The Private Lives of Pippa Lee." The next time you want to Google "how to take a fashion risk and execute it perfectly," simply consult this image. This is how you shake up the typically safe styles of a film festival.

9. Jennifer Connelly, 2010

We don’t sing the praises of menswear enough (just kidding: we try to do just that at least once a day), so it’s important to acknowledge the flawless execution of Jennifer Connelly’s dress-shorts-and-blazer ensemble. Bringing gentleman chic to the premiere of "What’s Wrong With Virginia," Connelly reminded us that you don’t necessarily need to wear a dress when you’re going formal – which might explain why so many women are now embracing that mantra.

10. Marisa Tomei, 2011

Metallic neutrals, a geometric pattern, and an unconventional shape: at the premiere of 2011’s "Ides of March," Marisa Tomei took a risk with even her hemline, making her dress seem more like an art print than a piece of clothing. But, unsurprisingly, it worked. Thanks to downplaying the accessory game (she’s not wearing any, minus her clutch), her dress offered both function and fashion, and almost seemed like a walking piece of 2014 jewelry.