Tele-retail fashion pioneer Diane Gilman built an empire out of selling jeans to the baby boomer generation. Not to mention she's currently Home Shopping Network’s longest running and No. 1 fashion personality, and the No. 2 vendor across all categories. Impressive, too, that her brand brings in more than $150 million in sales annually and has sold more than 9.5 million pairs of jeans to date. Well-done, Diane!

But c'mon. You don't get that far and that successful without knowing what women want. And Diane has hit on it more than once in this lifetime. While still in college, she opened a store on Melrose Avenue in Los Angeles that earned her an A-list clientele of Hollywood starlets. Throughout the 1960s and '70s, she designed custom denim for some of the music industry’s biggest stars. Then she relocated to New York City in the early 1980s and launched a collection of washable silks, the first of its kind in North America, which was quickly picked up by several major department stores. Her DG2 jeans' HSN debut was an instant success and sold 5,000 pairs within two minutes. She has since developed a loyal fan base and moves 200,000 pairs of jeans in a single shopping session (!).

Let's catch up with this indomitable femme to talk everything from how to shun stereotypes to the day Cher walked into her store in L.A.

How did you get into the jeans biz?

I often say my jeans saved my life, and the truth is, they've saved my life twice. First, in the 1960s, I started designing jeans as my Clarion Call of Freedom—at last, I could break out of the safe, cookie-cutter designs of the 1950s. Hand embroidery, dyes and rinses, rock 'n' roll ragged edges—that tough and sexy look represented rebellion and freedom.

Decades later, when I was in my late 50s, I sought rebellion and freedom again—this time from the matronly fashions women of my age were being offered as our only choice. I longed to feel sexy again. I longed to feel good in my jeans, like I did in the '60s. This led me to create jeans with stretch and style and new technology that make baby boomer women look and feel great. My DG2 jeans represent hope in a pant leg.

You’ve designed custom denim for some major names like Cher, Janis Joplin and Jimi Hendrix.  Is that intimidating in any way, or did you see it all as just another day?

Yes and no. When I designed jeans for Janis, she was just starting her career. I met her at her very first audition for record agents, at the famous Whisky A Gogo on the Sunset Strip‎. She was a brilliant wild child, the perfect model for my handmade jeans. Designing for her was fascinating, but not intimidating.

On the other hand, when Cher pulled up to the Los Angeles clothing store I had with a couple friends in 1967—called I'm a Hog for You, Baby—in her chauffeured white Rolls-Royce, that was intimidating. She took a look around, then yelled out, "Sonny!," and they bought out our entire store of A-line hippie dresses.

What advice would you give to other women who want to launch a brand?

Go with your heart, not your mind. Powerful, deeply personal niche ideas are where success and growth is today. My brand is a perfect example. I had very personal fashion needs as a middle-aged woman. I wanted to wear jeans and feel good about my body again, and I believed millions of women must have been experiencing the same frustrations. That intuition built a $100 million brand.

What's one thing do you wish you could have a do-over on?

That's a tough one. Maybe I wish I would have recognized my own power earlier in my life, but then again, having my greatest success come later in life—selling 10 million pairs of jeans and building a denim empire in my 60s—has a very special and uniquely satisfying quality to it.

What advice would you give women when it comes to their denim collection?

Go for a fashion statement, but assess what‎ you want and need. I think, many times, we get too caught up in runway rather than reality.  

I love how your book, Good Jeans: 10 Simple Truths about Feeling Great, Staying Sexy & Aging, addresses feminine stereotypes—what mistakes do you think women make when it comes to aging?

Many women give in to the myth that aging equals old, and nothing could be further from the truth. Women today have so many fashion and beauty options to reshape the vision of what 50, 60, 70 and beyond looks like. It's important to own where you're at. Give yourself permission to write your own rule book and love yourself.

It may sound corny, but ‎I have made my own rules my whole life, and I am in the middle of transforming my look and life yet again. After six months of chemotherapy for breast cancer that my doctors tell me will be completely cured by year's end, I lost my signature auburn hair. I depended on my long mane of hair—in red, the color of my youth—to make a fashion statement.  But when it was gone, I decided to create a new signature. My hair has started growing back in and it's pure white! To my surprise, I love it. I look at it as an opportunity to put together a new, individual look—one that's still chic, sexy and me.