At the Roosevelt Hotel in Manhattan last week, Roslyn S. Jaffe, the 85-year-old diminutive cofounder of Dress Barn, was dressed for success in a pin-striped suit, though it wasn’t from Dress Barn.

This story first appeared in the October 31, 2014 issue of WWD. Subscribe Today.

“I don’t fit into Dress Barn,” Mrs. Jaffe said. “People my age can absolutely wear Dress Barn. It’s just a size problem for me now. I’m not a size.” The occasion was the inaugural Roslyn S. Jaffe Awards annual luncheon, honoring Mrs. Jaffe and several “everyday heros” who help women and children in need through special programs and services.

It was also where Dress Barn, a division of the Ascena Retail Group, tipped its hand on an upcoming designer collaboration campaign called DressBar. Among the crowd of 498 were Heidi Weisel, Carmen Marc Valvo and Michael Smaldone from Adrianna Papell, who have all begun designing dresses for DressBar, which will debut next spring and be officially unveiled next month at the Highline Stages. “It’s about bringing runway-quality style and inspiring fashions to our value-oriented customers,” said Jeffrey Gerstel, the president of Dress Barn.

Soledad O’Brien, serving as emcee, wore a navy crepe Carmen Marc Valvo dress from the DressBar collection. Others present were Ruben and Isabel Toledo, who designs for Lane Bryant as part of her repertoire, as well as David Jaffe, Ascena’s chief executive, and members of the Jaffe family.

Addressing the crowd, Mrs. Jaffe said, “The name Ascena, it means nothing. But we have made it something meaningful.” She was referring not only to the company’s growth into the $5 billion operator of Dress Barn, Lane Bryant, Maurices, Catherines and Justice but also to its charitable spirit on that day: Ascena bestowed a grant of $100,000 to Aza Nedhari, executive director and cofounder of Washington, D.C.-based Mamatoto Village, which provides maternal services to low-income women of color; $25,000 to Evainna Ross, executive director of The Sparrow’s Nest, a program for underserved youth in Greensboro, N.C., and $25,000 to Joy Bergfalk, founder of Project Empower and executive director of the affiliated Coffee Connection shops, which provide employment training and support for women recovering from addiction. Other $5,000 grants were announced at the luncheon, which raised $600,000.

“Roslyn’s been at my side for the past 62 years,” said Elliot Jaffe, Ascena’s non-executive chairman, Roslyn’s husband and David’s father. “She’s the mother of three, the grandmother of five, and, most importantly, she gave me a job 52 years ago, when we opened the first Dress Barn.” It was in an old shoe factory in Stamford, Connecticut. “I took the first floor,” Mrs. Jaffe told WWD. “It had a little bullpen for the women to try on clothes, and we sold this one lined crepe dress from Jonathan Logan for $5.99 in red and black. The real value was $8.99. Everything we carried was first quality.”

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