From Inspiration to Impact: Why Kimberly Charles Chose Dress for Success
In honor of our 20th anniversary, we're sharing a perspective from Kimberly Charles, Dress for Success San Francisco/San Jose Board Member, who served from 2014 to 2016.
From left Kimberly Charles; Kimberly with long-time friend and Dress for Success San Francisco founding board member, Andrew Freeman, who introduced her to the organization; and with Vicki Liviakis.
When Kimberly Charles, founder of Charles Communications Associates, first attended a Dress for Success San Francisco event, she didn’t expect it would lead to years of involvement with the organization.
She was invited by her longtime friend Andrew Freeman, a founding board member of Dress for Success San Francisco and the organization’s 2022 Success Honoree. Freeman encouraged her to attend an event and experience the mission firsthand.
What she saw that evening made a lasting impression.
Not long after, she joined the Board and served for two years, bringing both her communications expertise, strategic insights, and her commitment to helping others.
A Lesson in Service That Started in Italy
Kimberly’s dedication to service began long before she became involved with Dress for Success.
When she was sixteen, she spent time working for the U.S. Navy’s Morale, Welfare and Recreation Office in Sardinia, Italy as her family was stationed there. Her boss was a woman named Giannina, who had devoted her life to helping others, eventually volunteering to work alongside Mother Teresa in India, in some of the most challenging human conditions for service.
Watching Giannina’s generosity and humility changed the way Kimberly saw the world.
The experience left her with a clear sense of purpose.
“I've always believed the rest of my life will be dedicated to helping those less fortunate than myself,” she said.
That early lesson stayed with her as she built a career in communications and marketing while remaining active in charitable work.
Discovering Dress for Success
Years later, Andrew Freeman introduced Kimberly to Dress for Success.
After attending her first event and hearing directly from a client speaker, the organization’s impact became clear.
“When you get a really moving client to speak, there's no better way to demonstrate the effect and power of this organization,” she said.
That moment confirmed her instinct.
“I'm in the right place.”
She joined the board in 2014, serving during a period when the organization was expanding both its programming and its community reach.
Bringing the Mission to Life
One of Kimberly’s most memorable moments during her board service was co-chairing the organization’s 2016 Success: You Wear It Well Gala with Andrew Freeman and Deborah Harrison.
Held at The Battery Intercontinental Hotel in San Francisco, the event combined fashion, storytelling, and philanthropy to celebrate the women served by Dress for Success. The evening included a runway fashion show and featured speakers such as Instagram COO Marne Levine and U.S. Treasurer Rosie Rios. “The room was electric,” she shared. “We had women on the rise and women of high achievement there to uplift and support them.”
For Kimberly, events like this helped people truly understand the organization’s impact.
Supporting Women Beyond the Suit
After her time on the Board, Kimberly continued to support the organization as a host committee member and donor, seeing the chapter evolve to provide broader career support for women entering or returning to the workforce.
“Bearing witness to the evolution of the programming over the years has just been a great delight,” she said. “It went from simply suiting to what I call continuous improvement, really being a holistic system for women.”
Why Giving Back Matters
For Kimberly, volunteering is about connection as much as impact.
“When you make time to help an organization and a cause such as this, it helps you probably by a factor of five times,” she says.
“It's enriching, it's rewarding, it connects us.”
Confidence Is the Best Accessory
Professional attire can open doors, but the real transformation happens when women gain confidence, support, and opportunity.
“Access is the only barrier,” she says. “Success belongs to everyone and everyone deserves it.”
Years after her board service ended, Kimberly remains closely connected to the organization — attending events, supporting its mission, and continuing to champion the women it serves.
Because sometimes a single introduction, a powerful story, or one moment of inspiration can lead to a lifetime of impact.
Dress for Success San Francisco and San Jose is a leading resource for advancing women in the workplace. Our purpose is to empower women to achieve economic mobility by providing a network of support, workplace attire, and development tools for success.