Not long ago, Olivia Chow says with a laugh, "the ladies" on her staff went through her closet and threw out half of her clothes. Too dated, decreed her press secretary and a campaign volunteer, for the wardrobe of a candidate for Toronto's mayor in 2014.

Ms. Chow has been striving to update her political image, too. In meetings on Bay Street and in private homes in Rosedale and Yorkville, this long-time stalwart of city council's left, then the federal NDP, is trying to persuade Toronto's establishment that it is wrong to write her off as a left-wing zealot, or pigeonhole her as a tax-and-spend profligate. Instead, she argues, she is a practical politician who would guard the public purse as closely as any conservative.

She points out that the leaders of her campaign advisory committee include philanthropist Margaret McCain, of the wealthy McCain food empire, whom she approached after joining the race, and Richard Peddie, retired chief executive of professional-sports juggernaut Maple Leaf Sports and Entertainment, who publicly urged her in January to throw her hat in the ring.

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She has promised to keep property tax increases no higher than the rate of inflation. "I'm not running a revolution," Ms. Chow says with another laugh. "We live in a free-enterprise system."

In a question-and-answer session last month in the board room of a Bay Street investment firm, she talked about how, as a city councillor, she fought to control rising police costs. At a political dinner for movers and shakers at the Grano restaurant on Yonge Street this week, she spoke about how her experience as a struggling immigrant from Hong Kong taught her thrift.

If there are property barons in the room, she reminds them that she has often worked with developers to approve big real estate projects in her downtown district. She even talks about making Toronto a North American hub for trading in the yuan, the Chinese currency.

In Ms. McCain's Rosedale residence, she spoke to about 40 people, most of them friends and acquaintances of her host. "I will talk for 10 minutes and the next 40 minutes they ask any questions they want," she says of her forays into boardrooms and living rooms.

"At the end, they make their own decision and that's how I win them over," Ms. Chow says.

She insists she is not abandoning her principles or renouncing her past. "Everyone knows I am a New Democrat. I am not hiding it," she told me. After all, "I was married to the leader of the party." She says she is just trying to show that the stereotype of the spendthrift NDPer does not apply to her.

"We are going [against] type," says Chow spokesman Jamey Heath. "It's not good enough for a progressive candidate to say: 'I don't hate business, I want to work with business.' We have to actively prove the point."

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The fact that Mr. Peddie and Ms. McCain have come on board as co-chairs of the campaign, he says, is "sort of our nod to the business community and to Toronto's establishment that they don't have to worry."

Don't they? Both an open mind and a healthy skepticism are in order when listening to the pitch of the new, more moderate Olivia Chow. Despite the image-softening exercise, this is the same Olivia Chow who told the anti-capitalist crusaders of the Occupy movement in 2011 that "We know that the rich – the 1 per cent – has gotten so, so rich and the rest are just really struggling to get by"; the same Olivia Chow who in 2008 denounced "ripoffs" by big banks and oil companies; the same Olivia Chow who in 2007 said Canadians were being "gouged daily" by high interest rates on their credit cards while the banks enjoyed "huge profitability."

Is such a consistent critic of corporate tax cuts and the big banks fit to lead the government of Canada's business and financial capital? Would she be beholden to the entrenched unions that support her if she became mayor? Would she let the city's recovering finances slide into disarray?

Ms. Chow is facing lots of questions like those as she makes her rounds. Suspicions of the NDP veteran run deep. Memories of the last left-leaning mayor, David Miller, are not fond in the city's glass canyons. John Tory, a former business executive, calls Ms. Chow "the NDP candidate" whenever he has the chance.

But with her new, moderate message, she has been winning over at least some Bay Streeters.

"I thought she came across as less of an ideologue than I would have thought," said Dave Samuel, a partner in the investment firm Birch Hill who set up a lunchtime session with her last month and now counts himself as a Chow backer. Another participant, a senior Bay Street lawyer, said he was "very, very favourably impressed with her, and I am a dyed -in-the-wool conservative."

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She told the group that she is the only one of the leading three candidates for mayor to oppose the Scarborough subway project. She favours a cheaper light-rail line instead.

"That is completely against the stereotype," she says. "I am the one who has the guts to say, Don't do it. Don't borrow money you don't have if you don't have to."

Ms. Chow will make her case to be taken seriously as a responsible manager in a speech to the Economic Club of Canada on June 17. Title: Creating jobs through smart economic development.