Cool Older Women Have This One Trait in Common

Gilman revolutionized the blue-jean industry in 2008 with her stretchy DG2 jeans for midlife bodies on HSN.

“Cool girls need cool jeans,” the “Jean Queen” told me a few years ago, while we were writing her memoir, Too Young to Be Old. She now has a podcast of the same name, full of advice on how to be forever cool.

Gilman stitched embellished jeans for cool icons Janis Joplin, Jimi Hendrix and Grace Slick. She’s got a big mane of white hair and a fondness for mixing pricey designer blazers with her affordable DG2 jeans.

“What makes a woman cool?” Gilman pondered. “Authenticity, gratitude, joy and living your life with purpose. ‘Cool’ is something you are — how naturally your personal lens interprets the world around you. ‘Cool’ is an innate, born with it, forever thing.”

Her own inspiring Queens of Cool include Keaton, Meryl Streep, Jane Fonda, Sarah Jessica Parker, Helen Mirren — “women who don’t deny their age but don’t give in to it.”

These women all seem to have that Superpower of Personal Autonomy — although Fonda admits it took her a long time to grab hers.

“When I was about to turn 60, I realized that I was approaching my third act — my final act — and that it wasn’t a dress rehearsal,” Fonda, who turned 88 in December, told Glamour magazine in 2022. She reviewed her life, her decisions and her tendency to please men, and then moved forward into her most powerful — and cool — act yet: being totally herself.

Fonda is now braver than she’s ever been, a far cry from her “shy” younger self.

Keep in mind: cool people who appear to be extroverted may actually be quiet souls who save the display for the stage. Edgy and powerful, Bruce Springsteen describes himself as introverted — although his stage persona “is pretty alpha-male, which is a little ironic, because that was personally never exactly really me,” he told NPR’s Terry Gross in 2016.

What looks cool? A signature style. Note that Diane Keaton’s look was quite defined — all black or all white, long sleeves, layers, big belt, hat — even while her personality appeared haphazard. This dichotomy added to her cool.

“She turned hesitation into style and self-doubt into art,” the staff at the jewelry brand Waxing Poetic, which specializes in the big crosses and chains Keaton favored, wrote on Facebook when she died.

Elegance can be cool. Fred Astaire and Josephine Baker were cool. Miles Davis recorded “Birth of The Cool” in 1957 — and the jazz great said he never left his house without looking “sharp as a tack.”

Of course, being an authentic nerd can be quite cool, too — just ask Jeff Hiller, who recently won an Emmy for playing the pure and authentic Joel in Somebody Somewhere.

And me. I’m an authentic nerd — and I’ve been owning it since I was in the eighth grade and my science teacher called me “sleepyhead.” I was a top student and far from sleepy, but she didn’t understand me because I am an introvert. I remember sitting at my desk and telling myself: “You’re as smart as anybody else. Speak up.”

I showed the world what I knew I was: a confident girl who followed the rules most of the time — but rebelled at any sign of injustice. Three years later, at 15, I got my first newspaper job.

Hey, science teacher, you don’t own me.

I decided to stand out in my style choices, too, determined not to fade into the background. Like Keaton, who wore two linen skirts to pick up her best-actress Oscar for 1977’s Annie Hall, I love to layer. My go-to staples: cinched vests with flowy maxi skirts and my Frye boots from 1984.

So, what’s not cool? Comparing yourself to anyone else, caring too much about what other people think, twisting yourself in a knot to please other people or “floating like a leaf through life,” as Fonda has said.

And which Jane is the coolest of all? Journalist Sarah Green Carmichael shared her choice shortly after Jane Goodall, the renowned chimpanzee expert and conservationist, passed away on October 1.

“Jane Goodall is the coolest person I’ve ever interviewed, and I’ve interviewed hundreds of people,” said Carmichael, editor at Bloomberg Opinion.

Why? Goodall practiced the Superpower of Personal Autonomy — she knew her purpose on this planet, and she acted on it.

A Netflix interview with Goodall, “Famous Last Words” — which she filmed in March 2025, knowing it would be released after her death — is a tutorial on how to be cool. In it, she leaves a final message:

“I want to make sure that you all understand that each and every one of you has a role to play,” Goodall said. “Your life matters, and you are here for a reason … every single day you live, you make a difference in the world, and you get to choose the difference that you make.”

You choose. That’s what makes you cool. As Diane Keaton (or Annie Hall) might say: La dee da, la dee da, la la …

 Which older woman do YOU really look up to? Let us know in the comments below.