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Features | Feb. 2025

WINE, WOMEN & SHOES

By Michelle Crowe

PHOTOGRAPHY BY RUNVIJAY PAUL
STYLING BY THERESA DEMARIA
HAIR AND MAKEUP BY LEANNA ERNEST

Ann wears a dress by Lulu Studio from Neiman Marcus in a friend's lovingly restored mid-century Hinsdale home.

70 Wine, Women & Shoes

In 1988, the idea to provide housing and intensive life-skills mentoring to families facing homelessness was met with a degree of skepticism. Many doubted that two businessmen could change how the community responded to and served families experiencing homelessness.

But Mark Milligan and Bob Wahlgren created a visionary model, by not only renting an apartment for a family in need but also joining each family with a volunteer mentor and professional case manager. This powerful strategy launched Bridge Communities, which has changed the lives of thousands.

Bridge has grown and expanded its services during the past three decades, but the commitment to creating change in the lives of families experiencing homelessness has never wavered.

70 Hl2025 02 082 L1014730
Ann looks forward to Wine, Women & Shoes wearing a Loewe dress from Neiman Marcus.

Bridge Communities has become a regional and national leader in transitional housing, as well as the surrounding issues that lead to homelessness, such as lack of affordable housing and well-paid labor jobs. Bridge Communities has counseled many organizations on establishing a transitional housing program based on this innovative model.

Prior to Ann Pitcher’s term on the Board of Directors, she and her husband served as mentors to two different Bridge Communities families. She calls the experience, “The best, hardest thing we’ve ever done.” The weekly meetings included going over expenses, making a budget, and coaching these working mothers on earning more money through promotions or finding a new job.

“That’s really the core difference with Bridge Communities. Lots of organizations can raise money by throwing big events but the relationship between the mentors and the clients is every week and that accountability is what makes the clients successful,” she says.

As big events go, though, this one is a winner.

“What’s not to like about an afternoon of day drinking, being with your friends, lunch, and a fashion show?” Ann asks.

Entertainment will include two talented young women singing duets from Wicked and the awarding of prizes for best shoes, boots, and other fabulous footwear. The winners will walk the runway so everyone can admire their good taste.

A graduate of Bridge Communities will speak, sharing her experience from the heart.

The room is full of women and moms listening to a fellow mother much like them who has lost her home, often to domestic violence. Ann says, “These women are employed and have at least one child. They never expected to find themselves in this situation, but now they must find their way through it. Their kids are in school, they’re packing lunches in the morning and trying to make a better life.”

70 Hl2025 02 081 L1014742
Ann wears a dress by Lulu Studio from Neiman Marcus in a friend’s lovingly restored mid-century Hinsdale home.

She reflects, “Family homelessness like this, people don’t even know it exists. Couch to couch family member to family member. It’s women who look very much like us and you can hear a pin drop when the speaker shares her story.”

Wine, Women & Shoes is in its fifth year. This dynamic day creates wonderful memories for those who attend and lasting impact for the families of Bridge Communities. Tickets sell out quickly as many want to be a part of this lively day.

“Invite your friends, get dressed up, and join the fun,” Ann says.

Wine, Women & Shoes is Saturday, March 8 from 11 a.m. – 4 pm at Oak Brook Hills Resort. Tickets are available at bridgecommunities.org.

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