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How 'Jean Queen' Diane Gilman hit reset on her career at age 58 and built a $100M brand

Gilman, 75, doesn’t intend to slow down anytime soon. “It feels like such a waste that you get to a point in a career that you have a history of success, the knowledge … and then your career is over with? That's just not for me."
Diane Gilman is an American clothing designer and shopping channel television personality on HSN.
Diane Gilman is an American clothing designer and shopping channel television personality on HSN.Claudia Paul

Diane Gilman may be 75 years old, but her working days are far from over. Gilman, otherwise known as the “Jean Queen,” has sold 17 million pairs of jeans in the last 14 years — and 2020 was her best year yet.

Gilman succeeded by championing a segment of consumers that had previously been ignored: women who are mid-life and beyond. Aside from clothing, Gilman is passionate about encouraging women to feel proud of the years they’ve accrued, not ashamed of them.

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“Women of a certain age don’t like to try on jeans in a store. Especially because the salesperson is 20 years younger and looking at you like an alien,” she said. By selling her collection on television, she said she can speak directly to women over 40 about the jeans she designed to flatter their bodies. She has been on air for 27 years and doesn’t intend to slow down anytime soon. In fact, she currently has a small studio set up to film right from her Manhattan apartment.

Gilman told Know Your Value: “It feels like such a waste that you get to a point in a career that you have a history of success, the knowledge to build a business, you know how to avoid mistakes…and then your career is just over with? That’s not for me.”

Getting started

A southern California girl, Gilman spent the 1960s and 1970s in Los Angeles as a local artist and "the ultimate cool girl hippie." She met rock stars while attending auditions and parties with her record agent boyfriend, and eventually musicians handed their denim to Gilman for her to hand paint, bejewel, rip, dye, or embroider. But when she tried to make a living as a clothes designer on the New York fashion scene, she didn’t have the fashion education to land a job. Instead, she started as a Bloomingdales salesperson at the age of 26 in the section targeting older women: “I was selling bullet bras before Madonna made them famous,” Gilman joked.

A chance conversation with her manager led to Gilman showing her collection to the decision-makers at Bloomingdales and the Abraham & Strauss department stores, who were extremely interested in purchasing her designs. Upon hearing the news, Gilman burst into tears because she didn’t have the financing to produce the product. Bloomingdales ended up funding her first and second collections.

Within five or six years, her clothing was prominently displayed in the window of every department store in Manhattan.

Getting seen

Gilman made her name known nationwide in the mid-1980s by introducing washable silk to America—first in stores, and then on television.

Even though Gilman had no hosting experience and described herself as being “image-phobic,” she didn’t shy away from the opportunity to sell. She knew nothing about hair, makeup, or studio lights, but said, “I liked the camera. I liked that it never talked back to you.”

Working to hone her telepresence, Gilman learned about rhythm and timing while on air. She hired an opera singer from Juilliard to teach her to lower her high-pitched voice. And more importantly, she defined her role in what she called “fashiontainment.” “Women may be sitting home alone…bored, depressed, anxious. We are there to inform them but entertain them at the same time,” she said.

Washable silk was selling well for Gilman, but there was just one problem. “It wasn’t what I wanted to wear,” she said.

Getting specific

“One day at 58, I looked in the mirror and thought this must be the wrong mirror to look in—you’re overweight, you’re over-age, and everything had dropped,” Gilman said.

In an effort to recapture some of her youthful vitality, she began searching for a “killer” pair of jeans. When she came up short after months of looking, she hit up her sample room, grabbed denim and spandex, and used her body measurements to create a custom pair of jeans.

Gilman laughed as she remembered the difference between her years of wearing “hide me” clothes, and that first walk down the street in her custom jeans when two construction workers approvingly yelled, “Get it going, girl!”

“If one jean makes me feel that good, and reconnects me to humanity and my youth, wouldn’t this work for millions or middle-aged women who were about to give up, like me?” Gilman wondered.

She shopped the idea around, but said it was received “like kryptonite.” She was even given feedback that “nobody wants to see a fat old chick in a jean.” But nothing could stop her drive. “Even with everyone putting the idea down, I couldn’t be moved. I couldn’t be discouraged. I knew I was right,” said Gilman.

After a year of requests, Gilman was granted air time to sell her jeans by Home Shopping Network CEO Mindy Grossman—on a Sunday morning at 5 a.m. in the middle of February, a time slot that Gilman called “deadly.”

She sold out all 5,000 pairs of jeans in three minutes.

Getting authentic

With a $100 million-dollar brand on HSN, strong international sales, a weekly televised fashion program and a book under her belt, Gilman could just rest on her laurels. Instead, she is as involved as ever in running the daily operations of her company, she’s writing a second book and she’s about to launch an entirely new business.

She said that it’s “unheard of” to be so successful in the fashion industry after the age of 60; there are really no models to follow. She’s hoping to continue blazing a trail for women in a very authentic way. In November of 2018, she even appeared on air immediately after her last radiation treatment for stage three breast cancer. Her trademark red mane may have been gone at the time, but her spirit was intact.

“I got off the table after my last radiation treatment and went straight to the airport to film,” she said. And her customers appreciated her all the more for it.

To other women who are hoping to make a change in their career at mid-life, she said, “Just give it a try. You can’t win it unless you’re in it. So if you feel like you haven’t hit your stride yet, stay in the game.”