The Style of Staying True

Goodbye Diane Keaton

“Something’s lost, but something’s gained
In living every day.”
— Joni Mitchell, “Both Sides Now”

Before we dive in this week, I just want to say thank you for all the comments, emails, and stories you shared on last week’s post about saying no. I was blown away by how many of you related (and taught me a few new strategies!). It’s comforting to know I’m not the only one still learning the art of “no” — boundaries really are a lifelong practice.

I had planned to write this week about milestone birthdays — specifically, turning 70. Several friends are approaching that landmark, and I’ve been fascinated by how differently each one is processing it. But then I heard the news that Diane Keaton had died, and everything shifted.

Now, before you start to worry, Leaving Middle Age isn’t turning into a “celebrities who’ve left us” column. (I did just write about Robert Redford!) But sometimes someone who shaped how you see yourself — or even how you show yourself to the world — leaves us, and it feels personal. Diane Keaton was that person for me.

---

When Annie Hall came out, I was in high school. I loved the movie, but what really stuck with me was Annie’s (really Diane’s) style. I had never seen anything like it — the hats, the vests, the ties, the slouchy pants, that mix of confidence and whimsy. It was revolutionary.

At the time, I was teetering between “fashion” and “personal style.” I didn’t yet understand the difference. But something in Diane’s look — that sense of complete ownership — lodged in my brain.

Looking back, it makes perfect sense that the brands I was drawn to (and later worked for) — Banana Republic, J.Crew, Levi’s — all aligned with my own developing taste. As I wrote in last year’s Party Dressing at Middle Age:

“Your style should be easy to articulate. I suggest narrowing it down to three words. My three are Easy, Effortless, and Elegant. I don’t do fussy. Bows, ruffles, endless layering, and loads of colors or patterns are just not me.”

So how does someone like me — who avoids bows and endless layering — end up naming Diane Keaton as a major style influence? Because she taught me the most important lesson of all: the difference between fashion and style.

---

Diane loved fashion — she played with it, collected it, and clearly delighted in it. But she never let it define her. She created a signature look early on and never let it go. Even when it was out of step with trends, she owned it so completely that it became timeless.

Over the years, her style evolved. It became more pared down, more architectural, more refined — but always her. The oversized belts, the wide-brimmed hats, the monochrome palettes — all still there, just quieter somehow.

And that’s what resonated with me most as I got older. The way she evolved her style without abandoning herself. That’s something I think about a lot now: how we adapt to our changing bodies, our shifting lives, and still stay true to who we are. (I would absolutely wear every look shown in the photos in this post EXCEPT the one from Annie Hall!)

I’d love to know — have you noticed your own style evolve as you’ve aged? Have you found yourself simplifying, or becoming bolder? Or maybe just more yourself?

---

I came across this quote from Diane in a 2012 AARP interview, and it stopped me:

“I never understood the idea that you’re supposed to mellow as you get older. Slowing down isn’t something I relate to at all. The goal is to continue — in good and bad, all of it. To continue to express myself, particularly. To feel the world. To explore. To be with people. To take things far. To risk. To love. I just want to know more and see more.”

Reading that now, I realize she wasn’t just talking about creativity — she was talking about identity. About continuing to show up as yourself, in every season, in every outfit, in every chapter.

Isn’t that beautiful? That word — continue — might be my new favorite.

We talk so much about “reinventing” ourselves as we age, but maybe it’s less about reinventing and more about continuing. Continuing to express, to explore, to take risks, to love. To keep showing up as ourselves — just with a little more clarity, and maybe better eyewear.

---

So this week, instead of a post about turning 70, I’m thinking about continuing. About staying true to ourselves, even as everything around us changes.

Thank you, Diane Keaton, for showing us that style is not about keeping up — it’s about keeping on.

If you have a favorite Diane Keaton look — or even a photo of yourself channeling your own “Diane moment” — I’d love to see it. Drop it in the comments or reply to this email. Let’s make this one a conversation.

Much love!

Thanks for stopping by Leaving Middle Age! If you found this interesting, please share it with friends, family, or anyone who’d appreciate the journey.