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For her Christmas concerts at Roy Thomson Hall this Thursday and Friday, Cole is casting aside her usual pantsuits to slip into the long, fitted gowns and black gloves that were her trademark in the '80s and '90s.
But only for the holidays.
"I've broken free from the nostalgic look of the Trio days. My music has changed and so has my look.
"With the exception of the symphony shows," Cole adds with a throaty chuckle.
"For them I'm going to wear a gown 'cause I want to wear a gown."
For those who missed the era of the Trio, Cole's latest compilation, Treasures, is highlights of songs recorded by the jazz ensemble from 1989 to 1993.
The Trio -- Cole, pianist Aaron Davis and string bassist David Piltcher, who produced platinum albums Girl Talk and Blame It On My Youth, among others -- became renowned for their jazz takes on such classic standards as Johnny Nash's I Can See Clearly Now or Chaplin's Smile.
"Treasures is a cross-section of different things. It's a 'greatest hits' in a way. It also marks a change. I'm not going back to those days," the singer says.
Cole's Christmas tour takes her across Canada, ending Dec. 23 with a performance in Nanaimo, B.C.
But according to the 34-year-old Maritimer, it's her music that's done the travelling this decade.
"The music's gradually evolved, gone in a direction more toward production, more toward pop. Anything I do will be an extension of that."
Cole's musical history has certainly had its period of flux.
Five years ago, she expanded her ensemble of piano and bass to include guitar and drums. For her last album, Dark, Dear Heart, she paired with producer Larry Klein (best known for his work with ex-wife Joni Mitchell) to create a pop-energized album with horns, electric guitar and digitalized drum loops. And now Cole's jazz ensemble will combine its sound with the Toronto Symphony Orchestra.
But Cole argues that these changes haven't detracted from the minimalism she has always strived for in her work.
She notes that for the concert, Davis adapted songs for the symphony to maintain the simple, pure-toned approach of the jazz group.
"This has always been our concept: Don't play many notes but when you play them, play the s--- out of them. Simplicity is the strongest statement you can make and also the hardest."
Yet as much as emotive, bare-boned performance is a part of Cole's approach toward music, so is her black sense of humour.
Cole has revised Gershwin, Tom Waits and even a song from a Disney cartoon.
Die-hard fans of The Jungle Book would have been hard-pressed to place Cole's drawn-out, piano-jazz version of Trust In Me (included on Treasures).
In the Disney cartoon, the giant python, Kaa, hums a song to lull Mowgli to sleep before snacking on the little jungle orphan.
Cole took the lullaby a step further.
"I loved the whole hypnotic drive of it, the double entendre -- that you shouldn't trust him at all. I thought, 'It wouldn't be hard to make the leap and turn it into a more sexual, dark song than something just for kids, keeping it humorous at the same time.
"In other words, the song's perfect for me," Cole says, laughing.
Expect more of the same tongue-in-cheek, sexual innuendo during Cole's Christmas concert, planning on performing Santa Baby, Tea For Two and Mary Margaret O'Hara's Christmas Trees And Holly Leaves, among others.
"I like to challenge people's preconceptions of what songs are about. You won't hear sleighbells jingling or Frosty The Snowman but it'll definitely be a fun, intense show."