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As tech entrepreneur Michael Hyatt and his mother made their way through a pounding Toronto snowstorm to help out at a recent workshop for women struggling with unemployment, they wondered if the adverse weather would dampen attendance.

As sponsors of the event through their family foundation, the Hyatts were gratified to find that almost 100 women had arrived, by 8:30 sharp, for a series of tutorials followed by a job fair that drew a dozen of Canada's major employers.

The activities were organized by Dress for Success, a not-for-profit outfit that provides business attire and job-search skills to women who typically have a tougher time finding work – economically-disadvantaged single mothers, new Canadians, women trying to re-enter the job market after raising children or women over 40 who suddenly find themselves unemployed after years with the same employer. The goal is to help them achieve economic independence.

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"We're not doing this for the person who needs to become vice-president of one of the banks," said Mr. Hyatt, co-founder and now a director at software company BlueCat Networks Inc., a founding partner at the Rotman School of Management's Creative Destruction Lab, an investor and philanthropist. The Hyatt Family Foundation, which Mr. Hyatt chairs, aims to support organizations, such as Dress for Success, "where we can have the most impact on individuals." A global movement, with affiliates across Canada, the organization also serves men through its Dress Your Best arm.

In 2018, the Toronto affiliate of Dress for Success outfitted and provided career advice to 1,600 women. This year, the target is 2,000, said Andrea Elliott, chair of the board of Dress for Success Toronto and an international retail consultant.

It has become a popular cause with Bay Street professionals, who donate “gently used” business wardrobes, volunteer as mentors, or give money. This year, several Toronto organizations have invited Dress for Success to make presentations during the week leading up to International Women’s Day on March 8. The Toronto office of Fidelity Canada has designated Dress for Success as a “charity of choice” at its upcoming International Women’s Day event for employees and clients. A number of high-end retailers donate new clothing, and Toronto-based jeweler Jenny Bird, inspired by “the sheer determination and resilience” of former Dress for Success client Share Ryan, has designed a limited edition pendant to be sold in support of the organization.

Ms. Ryan, now a customer success manager at Toronto-based digital advertising firm StackAdapt, was a homeless 18-year-old in Ottawa when staff at the shelter where she was staying took her to Dress for Success.

In an interview posted on Jenny Bird's website, Ms. Ryan relates: "I don't know why, but they insisted that I try on a bold, red pantsuit. I put on the suit, found a full-length mirror and immediately burst into laughter. I had been wearing the same clothes for several months and neglecting my appearance overall, so this very polished, brightly-lit, Hillary Clinton-esque image looking back at me from the mirror was jarring to say the least."

Feeling rather overdressed, Ms. Ryan applied for and landed a job at a fast-food restaurant, survived on free hamburgers, saved money and put herself through a biochemistry program as McMaster University before earning a college diploma in advertising. In 2017, Ms. Ryan organized a clothing drive at her office for Dress for Success.

When women are referred to Dress for Success Toronto, their first stop is the organization’s boutique where, in a 90-minute consultation with a stylist, they put together two complete business professional outfits – including shoes, handbags, accessories and outerwear if needed. The next step is pre-employment counselling. Once they land a job, clients can return to the boutique to select three more outfits free of charge, Ms. Elliott said in an interview.

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The recent workshop attended by the Hyatts, geared to job-seekers over 40, included sessions on networking via LinkedIn, skills upgrading, job interview strategies and a chance for one-on-one interviews with employers from such organizations as management consulting firm Accenture, Bank of Montreal, Microsoft Canada Inc., the Government of Canada, confectionary firm Mars Canada Inc., Starbucks and Mackenzie Investments.

These organizations are hiring, Mr. Hyatt said, and many of the Dress for Success clients have the experience they are looking for. They just lack the connections to get a shot at speaking to a company like Microsoft.

This is one in a series of stories being published during the week of International Women’s Day.

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