Retail powerhouse Roslyn Jaffe remembers her childhood of modest means and her struggles as a working mom. Now, her philanthropy seeks to help those with few resources.

In 1951, Roslyn Solomon was in the management training program at Gimbels. Elliot Jaffe was a buyer at Macy’s. Although the stores were legendary rivals, the pair became anything but.

A marriage and three children later, even their common interest in retail came together. In 1962, Elliot came up with an idea for a business they could start on their own. He had noticed that many wholesalers of hard goods, such as televisions and appliances, were successfully opening discount stores and thought a discount concept for apparel could do just as well. Since they couldn’t be without Elliot’s steady paycheck, it was Roslyn, then a stay-at-home mom, who opened the shop: Dressbarn, a clothing store for the working women she understood so well, in Stamford, Conn.

Today, Dressbarn is part of a family of seven brands under the umbrella group Ascena Retail that includes Justice, Ann Taylor, Loft and Lane Bryant. The group brings in $7.2 billion in annual revenue and operates 4,900 stores with 70,000 employees. Though the businesses have made Roslyn Jaffe and her family wealthy, she says she has never forgotten what it was like to struggle as a working mother. Thirty years ago, she created the Jaffe Family Foundation to focus on helping women and children, healthcare and education services.

The foundation’s centerpiece is the Roslyn S. Jaffe Awards, which works with the Ascena Foundation to honor those “who are making the world a better place for women and children, specifically in the areas of health, education, social reform and esteem.” The grand prize winner receives $100,000, and two runners-up each receive $25,000. About 2,000 groups a year compete for the grants.

“We believe in helping those who need help,” says Jaffe. “We didn’t sit down and create a philosophical statement. We have a statement that we just have in our heads, that we want to help in many ways.”

The Jaffes also fund the Elliot and Roslyn Jaffe Food Allergy Institute at the Icahn School of Medicine at Mount Sinai in New York. Ascena has a philanthropic arm, Ascena Cares, which benefits even more organizations with a focus on aiding women and children, such as Dress for Success, the Police Athletic League and the American Cancer Society.

At 87, Roslyn Jaffe still participates in her family business as director emeritus, but she and her husband, who is chairman emeritus, have passed along most of the management to their children, David, Richard and Elise. They’ve also passed along something they consider just as important: the spirit of giving. Jaffe spoke to Worth about being a pioneering female executive, helping women in need and building a legacy for her children and grandchildren.

Q: Let’s start at the beginning. How did your business evolve?

A: At the time that we started the company our three children were 3, 5 and 7. Elliot was commuting to Macy’s every day. He couldn’t just drop his job and have no income. So I said, “Stay at your job, and I will work it out in some way.” David was in nursery school, Richard in kindergarten and Elise in second grade, and we scheduled our lives around that.

What was the business idea?

We would buy merchandise and discount it. Others were discounting hard goods, radios, TVs, refrigerators, and our idea was to discount clothing. Hard-good reselling was very successful, very quickly, so we got excited about this other concept. We thought, OK, let’s jump into this. We had energy and drive.

Who was the target consumer?

At the time women mainly wore dresses. Sportswear was very small and just coming into the professional world. What we were doing was dressing the teacher, the woman who works in the bank, the receptionist, because they were not wearing pants in those days. We started with dresses and then got into skirts and blouses, and then actually blazers and two-pieces like gray flannel suits.

“The big retailers on the street didn’t like us because we were discounters and that was a dirty word at the time.”

  • The Jaffes' first story opened in Stamford, Conn., in 1962.

Photos courtesy of Roslyn Jaffe

Did you know it would be so successful?

No. But we dreamed that it would become what it is today. Elliot [whose initials are ESJ] tells a story of when we first started having some success. He bought himself a second-hand Porsche. That was a really very big treat. And the license plate on it was ESJ10, which was his goal for the number of stores we would have.

How did you become a philanthropist?

We were residents of Stamford, and our store was off the main street, this tiny little store. We got to know our neighbors, like the restaurant nearby that served breakfast and lunch. The big retailers on the street didn’t like us because we were discounters and that was a dirty word at the time. But we had our customers, the working women. And one of the people we hired part-time was a woman who was a volunteer at a rummage sale kind of place where they raised money for hospitals by selling discounts and things that they were able to get from the stores. She told us about her volunteer work, and immediately whenever we had some damaged goods or something, whatever, she took it and sold it for the hospital. And so we started getting involved with the community through little things like that. 


Roslyn Jaffe at the Ascena offices in Mahwah, New Jersey. Photo by Jeremy Bales

Were you encouraged to be philanthropic as a child?

I was raised in Waterbury, Conn., in a family that did philanthropy in a very, very small way. We had little or no money, but in the house we had a box where you put money for charity (tzedakah in Hebrew), and my parents contributed in the community where we lived. It was something that I grew up with.

We started very early with the company. Obviously, it became important when we went public in 1982, and we had finances and decided we could have a foundation. That’s when we really had the funds to do bigger things.

What made you decide to focus on education and children’s issues?

That was my life. I was the third child. I was grateful that I could go to college because my brother got the GI Bill, and that meant there were some funds for me to go to college, which was a big treat. I had three children, and none of them was really healthy. There was a point where we went to a specialist at Columbia Presbyterian and could not afford his fee. We worked it out. So I was always very conscious of children and their needs, because I lived through some of it.

“I was always very conscious of children and their needs, because I lived through some of it.”

Did you ever want to underwrite the ballet?

[Laughs.] No, Elliot does that. He gives to Lincoln Center and the Guggenheim. Those are the two areas that he’s interested in. I have no great desire to have my name in lights, but he includes me as part of the contribution that he makes.

Did you come up with a philanthropic philosophy?

We didn’t sit down and create a philosophical statement. We have a statement that we just have in our heads, that we want to help in many ways. Each of our children has different interests, but they all center on health, education and children.

Tell me about your awards initiative. You give money to women whose organizations stand out through their own generosity.

We wanted to find people who needed help with their giving, who didn’t have the sophistication or the connections to expand what they were doing. It was like the way we started our small company. These people are starting small philanthropies, and we wanted to help them.

  • Vanessa Garrison of GirlTrek accepting the 2016 Roslyn S. Jaffe Award

Photos courtesy of Roslyn S. Jaffe Awards

Who are some of your winners?

GirlTrek—a three-year-old national nonprofit that empowers young African American women through daily walking—is the most sophisticated of all the winners we’ve had. It has more than 400 neighborhood volunteers who serve as role models, street organizers and leaders that promote public health. It won in 2016, and we’ve had people who wanted to connect with them right away. So they are really doing well.

Our 2015 grand prize winner was All Our Kin, which trains and supports community childcare providers in four Connecticut towns. The runners-up were Volunteen Nation, which connects teens with service projects and community-building organizations, and Polished Pebbles, which works with low-income girls in Chicago to teach effective communication and interpersonal skills.

All the organizations are grassroots, led by regular people, for whom the award you were giving would make a huge difference.

I wasn’t looking for a big PR thing. The big organizations can do big  fundraisers. These are the new people who can’t do that, and it was appealing to us that we could help people who were not as sophisticated, who needed a little push up. Even the $25,000 award has helped. The $100,000 award has helped a lot.

Now you’re building a network among your winners, right?

We are bringing the winners together. We have a two-day seminar with the winners, and we have speakers. So they meet one another and are able to support and give advice to one another.

How much do the different generations of your family get involved?

Right now the foundation is Elliot and myself and our three children. Eventually, I would like all the grandchildren to be involved as well. We have been very fortunate, and therefore we have to give back.

—With Rose Arce

For more information, contact: Sue Ross, Ascena corporate affairs, sue.ross@ascenaretail.com, 212.491.2110, ascenaretail.com; ascenacares.com

EXPERT

Soledad O’Brien
CEO | Starfish Media Group

Soledad O’Brien is an award-winning journalist, documentarian, news anchor and producer. She is the anchor of the weekly political magazine show Matter of Fact, which airs on Hearst TV stations around the country.