Search & Replace S03E10: Diane Gilman

Diane Gilman, known as TV’s Jean Queen, shares her journey of pursuing her lifelong passion for fashion design and combating ageism in the industry. Despite facing initial resistance from her parents and societal expectations, Diane fought for her dreams and gained recognition for her unique designs. However, as she grew older and faced personal challenges, Diane felt disconnected from her own fashion line. Determined to regain her confidence, she created a perfect-fitting pair of jeans for middle-aged bodies, which transformed her self-perception. Discover how Diane is helping women embrace aging and find happiness by pursuing meaningful activities aligned with their passions and skills on Search and Replace. 

More about today’s guest:  

Explore these related stories:


[00:00:00] Announcer: Support for the following podcast is provided by the user experience specialist at Johns and Taylor. More information follows this episode. 

[00:00:09] Joe Taylor Jr.: What if the mission you’ve pursued for your entire life suddenly seems unrealistic when you reach a certain age? I’m Joe Taylor, Jr. This is Search and Replace.

We might consider ourselves really lucky if we get one of those epiphanies about what we think we’re meant to do with our lives. Diane Gilman says she understood her life’s purpose at a very early age. 

[00:00:38] Diane Gilman: It was my destiny. You know, that was one of those things where you’re three years old and you’re picking up your first crayon and you’re drawing a stick figure girl with a dress and punching in polka dots. I was very particular, even as a three-year-old about what I was wearing that day to Pre-K and I would throw fits if I didn’t like it. It was an obsession and my parents did not think it was proper for an upper middle class little girl to even be thinking about working, or a career. 

There was no such thing as a career woman and nobody knew how to handle me because it was so odd to them. What do you mean you don’t wanna marry a doctor – second choice lawyer, third choice CPA? So I got very little support because this was not my parents’ vision. I had to fight for everything I did.

I think my guiding light my entire life was my absolute belief in my talent, even when other people didn’t see it. 

[00:01:58] Joe Taylor Jr.: And the people who did see Diane’s talent, rock and roll luminaries like Jimi Hendrix and Janice Joplin. Painting and embroidering jeans for celebrity clients in Los Angeles led Diane to move up the coast to San Francisco, where she styled the likes of Jim Morrison and Jerry Garcia.

Not long after another move to New York City, Diane’s first clothing label went on sale in Bloomingdale’s, followed by a collection on QVC.

Despite earning a reputation as TV’s Jean Queen, an unexpected turn of events left Diane feeling out of step with even her own fashion. 

[00:02:33] Diane Gilman: I got a really new body as I got older and I went up to 200 pounds. My husband passed away from cancer and I made food my companion and I couldn’t wear anything. I could barely wear my own designs. 

And I was designing because I introduced washable silk to America. So on HSN I was selling my washable silks, but they weren’t me. 

In my youth, sixties and seventies, I took denim from some of the rock and roll star grates, and I slashed them and painted them, jeweled them, embroidered them, patched them.

And I thought, why can’t I wear jeans anymore? That’s not right. It’s tired of me. I’m still that rock and roll chick. So I thought, you’ve got a design room in New York. Just go at him by three yards of denim, take your measurements, make yourself a jean. 

And I remember the first day I put them on to walk to work, I was walking down 34th Street to the Garment District. And there were two young guys and one of them looked up and he said, ‘Hey lady ya gotta going babe!’ And I’ll tell you what, it changed my life. I didn’t feel invisible anymore. I didn’t feel pushed aside anymore. I didn’t feel not listened to anymore. And I thought, wait a second. A perfect fitting pair of jeans for a middle-aged body is a passport to another life. 

[00:04:12] Joe Taylor Jr.: Diane’s business partner and even some of her previous distributors weren’t so sure about her instinct on this one. But selling 5,000 pairs of jeans in three minutes on HSN proved her idea, had an audience. But would that be enough for Diane to win over the rest of the fashion world?

[00:04:29] Diane Gilman: I thought, this is gonna change the fashion industry. Everyone’s gonna see that this is a huge niche business and we as baby boomers are the spending power of America. No. No. It was incredible to me that you could provide something that gave so much benefit to the customer, made them feel younger, more connected to their youth, more vibrant, more purposeful, more in it to win it. And yet other manufacturers still just wanted to make clothing for, you know, tiny little hundred pounds, six-foot tall, wish I was a supermodel, 18 year olds. Unbelievable. 

Although I was on the air for 30 years, the last 16 years were when I developed DG2 and selling over 20 million jeans. And still the industry just goes on doing what they’re doing. Unbelievable. 

So, you know, helping to alleviate ageism has become my new passion – cause I’m old and I don’t wanna be treated that way. 

[00:05:41] Joe Taylor Jr.: And that’s how the little girl who thought fashion design would be her lifelong destiny discovered a new mission in her third act. 

[00:05:49] Diane Gilman: I’m finding my way in a whole new world that I really like and hopefully my legacy will be that I’ve been some kind of significant help to women accepting aging, seeing it as an advantage, as a plus, and understanding you can work with it. You have a right to be happy. And you also have a road to happiness. You just may not be able to see it right now, but find it. 

And if you’re older, take all the skills you accrued all your life and find something wonderful to do with them. And don’t expect anything from corporations, by the way. There are so many arenas that don’t respect our age. But find something you truly from your heart believe in and love to do, and it will find its own path. 

[00:06:43] Joe Taylor Jr.: That’s TV’s Jean Queen and the author of the book, Too Young to Be Old, the Diane Gilman. We’ve got links to Diane’s book and to other resources for planning and navigating your own third act in our show notes and on our website at

Today’s episode was produced by Nicole Hubbard with help from the entire Podcast Taxi team. I’m Joe Taylor, Jr. 

[00:07:05] Announcer: This has been a Podcast Taxi radio production. 

Support for Search and Replace is provided by Johns and Taylor, user experience specialists serving media and technology companies that want their websites to work.

Learn more about how top performing businesses eliminate barriers between customers and their goals at

Joe Taylor Jr. has produced stories about media, technology, entertainment, and personal finance for over 25 years. His work has been featured on NPR, CNBC, Financial Times Television, and ABC News. After launching one of public radio's first successful digital platforms, Joe helped dozens of client companies launch or migrate their online content libraries. Today, Joe serves as a user experience consultant for a variety of Fortune 500 and Inc. 5000 businesses. Twitter | Facebook | Instagram

Leave a Reply

Your email address will not be published. Required fields are marked *