Confidence, Dignity, and Hope: Inside the Work of Dress for Success Orillia and Barrie

In Simcoe County, employment transitions can be isolating — particularly for women navigating job loss, career change, or re-entry into the workforce. When Linda Reid founded Dress for Success Orillia and Barrie, it was in response to a clear gap: there were no dedicated local services focused on helping women build confidence and access suitable professional clothing for job searches and interviews.

From the beginning, the work was never just about clothing.

“It’s true — when you look good, you feel good,” Linda explains. “But what we really see is the increase in confidence. That confidence is what carries women forward.”

That belief is at the heart of Dress for Success Orillia and Barrie’s programs, including The Breakfast Club, a free nine-week pre-employment program designed to support women who are unemployed, under-employed, or actively seeking work.

The Breakfast Club offers much more than job-search tools. Through weekly workshops — covering confidence building, communication skills, interview preparation, personal branding, and mental health during job searching — participants are given space to rebuild confidence, connect with others, and regain a sense of hope.

For Linda, success isn’t always measured by immediate outcomes, though employment is often achieved. Instead, it’s found in quieter moments. “When the women we serve tell us their confidence has increased — that’s success,” she says. "And of course, when they secure employment.”

Volunteers play a critical role in making this work possible. In fact, Dress for Success Orillia and Barrie is 95% volunteer-run, supported by one part-time staff member. Without volunteers, the organization simply could not operate.

But the work also relies heavily on community support. As a non-government-funded organization with no core funding, Dress for Success Orillia and Barrie depends on financial contributions from individuals and businesses to continue serving women in the community.

At its core, the organization is focused on protecting something deeply human. “We are preserving the dignity and hope of the women we serve,” Linda shares. One story continues to stand out.

A woman in her early 60s joined the Breakfast Club after losing a job she had held for 25 years— just three years before retirement. The loss deeply affected her mental health and sense of identity. Attending the Breakfast Club workshops gave her structure, connection, and hope. She later shared that the program saved her life. Within six months of completing the nine-week program, she found employment.

Stories like this are why Dress for Success Orillia and Barrie continues its work — quietly, consistently, and with care.

When asked what she wishes more people would ask, Linda’s answer is simple: “How can I help?”

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Dress for Success Orillia and Barrie is a nonprofit Her Community has partnered with through volunteer days, supporting the work they’re doing in the community.

If you’d like to be part of something like this, you can find out more about joining HER Community here.