My father was a custom tailor. My mother worked as a model on Seventh Avenue [in New York’s Garment District]. When I was a child, they would bring me there from our home out in Queens, and I said the one thing I never wanted to do was to be a designer! My dream in life was to sing like Barbra Streisand and dance like Martha Graham.

I was not a very good student in high school—I was good at the art world. I would sit in the art room all the time, often with [now world-famous artist] Ross Bleckner. I made my first collection while I was at George W. Hewlett High School in Five Towns on Long Island.

I went in to Anne Klein to apply for a summer internship after my sophomore year at Parsons School of Design, and Anne asked me to walk for her because she thought I was a model. When I showed her my portfolio, she said, “You’re hired.” Then Anne told me I should quit school because I was already a designer. I did.

I was pregnant and working for Anne Klein when Anne found a lump. She was sick. I was having a baby. We ended up in two different hospitals. The next collection was due. Anne and I were on the phone discussing how many buttons we want on a navy blue blazer coat. Six or eight? I had no idea she was dying, and I never saw her again.

I came up with the idea for Seven Easy Pieces at Anne Klein: a bodysuit, a wrap-and-tie skirt, a jacket, a coat, leather and suede, knitwear and an evening piece [above]. I was going to build that for them. Instead, they fired me and told me it was time to start my own business.

For a while it was the three of us, but I was the baby. Calvin Klein, oh my God. I had a crush on him. I will admit he was hot, is hot. We were so completely different. Calvin was more of a minimalist, very neutral and beautiful and worldly in color. Ralph was jeans, vintage shirts and ties. And I was all black. I could always tell who worked for who when staff got on the elevator, because of how they dressed.

I was told that Barbra Streisand had just bought one of my furs but needed the clothes to wear with it. I emptied my closets and brought everything to show her. I walk in, and she’s sitting there. I said, “I’m sorry, but I’ve just got to sit down. You have no idea, you are my dream.” And Barbra looks at me and says, “Do you have any clothes to go with these fur coats?” Fast-forward, now she’s my sister for life.

My daughter Gabby started taking all my clothes, wearing them to school—long velvet dresses with boots—in high school. That wasn’t cool. So I said, “I gotta make a younger person’s collection.” DKNY was born.

After the earthquake hit Haiti in 2010, the person running my studio, who was Haitian, persuaded me to go down there to help. In Haiti [above], I realized that many of my causes overlapped with Haiti’s needs—the preservation of its culture, the need for better health care. So I brought down integrative therapists from [her current brand] Urban Zen. I also brought my grad students from Parsons to learn and work with them. Over the years, I partnered with Haitian artisans who made accessories for Urban Zen, with the money from any sales going straight back to them.

It’s a top or dress with the shoulder cut out. The only place you never gain weight is your shoulder. Forget the rest of your arm! [Laughs] Hillary Clinton wore it when she was first lady, but it looks good on everybody.

I do Pilates and meditation. I was a major skier. As a result, I have a lot of breaks in my body. I have six screws in one knee, seven in the other. So what I need strong is my gut. And working on your gut is what you do in Pilates.

In a sense, I have always had this problem because most artists think from a different side of their brain, which is why I am so weak in learning computer technology. But memory loss still concerns me a lot. As we sit here today, there’s so much that I can’t remember, and it’s frustrating. Fortunately, I have visual memory. I can’t remember names very well, but I’m great with fabrics, shapes and color. —As told to Harriette Cole