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tiff 2011

Angus Rowe Macpherson for The Globe and Mail

It's natural to fret about dressing for the red carpet: During my four years on the party beat at the Toronto International Film Festival, which kicked off again on Thursday, I could handily pick out celebs swilling martinis from across a crowded room, but felt significantly challenged when it came to picking my outfits. Contributing to the conundrum was the fact that Toronto's film festival has never had a particular sartorial identity, unlike Cannes (where resplendent Croisette-calibre gowns are the norm) or Sundance (where the crowd eschews formality for denim and down jackets).

At TIFF, you might start the evening at a gala screening where little black dresses abound, move on to an industry event packed with men in leather jackets and women in jeans and photo-shoot-fresh Louboutins and, finally, cap the night in a dive bar rubbing elbows with Drew Barrymore as she throws back Stiegl beer in an Alexander McQueen frock (yes, this actually happened).

In other words, you can, in a matter of hours and a number of venues, be guaranteed to spot some combination of pouffy, slinky, edgy, trashy, pretty, scruffy and stuffy – and that's without factoring in a Tilda Swinton sighting, which, invariably, proves to be all kinds of awesome.

While dressing for the festival can be a challenge, though, the fact that Toronto hasn't locked down a look brings a refreshing freedom with it. "Everything works," Toronto-based stylist Roz Griffith Hall, who has primped a wide range of boldface names, insists of TIFF's party circuit. "Nothing is out of style unless it's worked terribly."

When it comes to TIFF fashion, Griffith Hall distinguishes it from Cannes or Venice by calling it "sassy," suggesting somewhere between rock 'n' roll and refined (think floral prints moody enough for evening or a pantsuit with a pair of killer heels) as the sensibility to both look for among celebs and emulate if you happen to attend events this year.

She also offers a neat dressing strategy: Consider the film when selecting the fashion. "I try to marry the look with the movie," she explains. (By this token, W.E., Madonna's flick about fashion icon Wallis Simpson, could be a fun one. Ralph Fiennes's Coriolanus? Not so much.)

Tanya Kim, co-host of the CTV entertainment show eTalk, has been reporting from red carpets around the world for much of the past decade. While she describes TIFF's sartorial trademark as "toned-down glam," she also notes that the stars who participate never take their garb for granted.

"With TIFF getting bigger and bigger – and this [year's]will be the biggest so far – celebs are no longer thinking that Toronto is just quaint and charming and laid back," Kim says. "I think [everyone]is embracing the glamour. And as the stars flood in, they're bringing that glamour with them."

What Kim likes most about Toronto is that people can see film royalty's personal style shine through; she cites a top hat worn by Sienna Miller in 2007 as an example.

For this reason, Kim recommends respecting the hierarchy and leaving the spotlight to the stars. "You don't want to look like you're trying to stand up one of the actresses," she says.

TIFF, though, is too celebratory to don something less than stellar, even if your name isn't the one up in lights. Some surefire ways, beyond the chosen outfit, to up the glam quotient: standout accessories, a killer manicure, a fun 'do. "The grooming and makeup is where it's at," Griffith Hall says. "Great shoes bring that little black dress into focus."

A note about heels: I suffered a stress fracture in my foot at the tail end of TIFF four years ago because I was adamant that flats wouldn't cut the mustard. But party hopping can be perilous in sky-high stilettos, so ditch your ego at the velvet rope or carry a change of shoes if hours schmoozing are greater than hours screening.

And here's one more tip that seems obvious until your credit card statement arrives: TIFF fashion does not take priority over paying rent. Winners, the Canadian destination for discounted fashion, unveiled its twice-yearly designer collection on Thursday, coincidentally coinciding with the festival's start. Translation: big-name brands and runway looks at up to 60 per cent off. Colleen Uncao, the company's fashion expert, says that women can expect to find full- and cocktail-length dresses, ace accessories and ultra-trendy footwear for less money than the cost of some festival packages.

Ultimately, TIFF offers an opportunity to think openly about special-occasion dressing. Kim, for one, is excited to both ogle and participate in the parade of fashion – but with a caveat. "As long as you don't look like you're hitting a Jersey Shore club, you'll look great," she says. "Stay classy, Toronto!"

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