Diane Keaton Left the Blueprint for Dressing. Now Use It.

by | Oct 20, 2025 | Style

Image: SFD Media/Getty

“Diane Keaton, arguably the most covered-up person in the history of clothes, is also a transparent woman. There’s nobody who stands more exposed, more undefended, and just willing to show herself inside and out, than Diane.”— Meryl Streep, AFI Lifetime Achievement Award, 2017

She taught a generation of women that clarity is the highest form of style.

Diane Keaton’s passing leaves more than a cinematic legacy. She leaves an action plan for how to think, dress, and age with deliberate intelligence.

In Los Angeles and on the Hollywood backlots, Keaton was undeniable. Bowler hat, long vest, an architecture of layers. She was performance art in motion: self-knowing and deliberate. At 79, she had negotiated a private armistice with the mirror—no apology, no need to be liked. She dressed like a woman mid-sentence, ideas still arriving.

Dressing as Argument

To call her a movie star is insufficient. Keaton was so many things: mother, director, photographer, preservationist, house-flipper, eccentric, architect of self. She taught our generation how to be messy and human. But her style? A blueprint for dressing that was not as much about audacity (although there was plenty of that), but more about intelligence. Her clothes worked for her as codes, strategy, subversion, connection teaching us to be grounded in what makes us ourselves.

Our favorite of her films, (Annie Hall, The First Wives Club, Baby Boom, Something’s Gotta Give) mark the decades, yet the real transmission happened in the repetitions—her editorial palette of black and white, boyish vests, coats cinched at the waist. She showed that dressing with intention isn’t a plea for relevance; it’s a quiet argument made on your own behalf. She noted in a Gloss interview that Annie Hall (for which she won an Oscar for Best Actress in 1978) stirred this reflection: “I look back on Annie Hall and can’t talk about that movie without talking about the fashion, it was everything to me,” she said. “I loved being able to dress like myself. My muses were the women of New York City who were walking the streets of Soho in baggy trousers and a blazer. I was layering pieces.”

Parallel Worlds: Disney and Diane

I learned to read clothing that way in the early ’90s, running costume design at Disney. I managed fittings for Belle and Snow White, negotiated fabrics and silhouettes, and kept characters recognizable from 20 paces.

While Keaton was filming First Wives Club, I was backstage at Disney, testing character heads, mermaid tails, and ridiculous shoes worn by a giant mouse. We were both designing visibility—mine commercial, hers fiercely personal. Unlike my gig at “The Happiest Place on Earth,” she didn’t perform fantasy; she dismantled the expectation that a woman must dress to explain herself. We worked with the same materials but my costumes were engineered for illusion, hers for clarity.

The Menswear Rewrite

Before Keaton, womenswear flirted with the masculine mostly as spectacle. Marlene Dietrich and Katharine Hepburn wore trousers when it was a provocation—proof that elegance could coexist with defiance. But Keaton made it practical, witty, approachable, and wearable. She translated rebellion into vocabulary. These early provocateurs made it sexy, but never for the male gaze.

I was 17 when Annie Hall premiered, weeks away from entering a military college—about to wear a men’s uniform meant to make everyone identical. Keaton’s trousers and ties rewrote that uniform into a manifesto. She even used her own wardrobe to build the character of Annie. Her high-waisted trousers, vests, and ties weren’t rebellion for rebellion’s sake; they were a visual shrug at a century of assumptions about who suits—or uniforms, for that matter—belong to.

She made tailoring soft and wit structural. Accessories became punctuation marks—a belt as boundary, a bowler as signature. Any woman who has held her ground in a conference room knows that style has its own grammar. She practiced feminism the way she dressed: without asking permission. Her restraint wasn’t apolitical; subtlety was her weapon. In a decade when second‑wave feminism demanded visibility, she demonstrated that self‑definition could be its own form of protest.

Visibility, Not Volume

For women over 50, the lesson isn’t to take up space so much as calibrate it. Composition beats camouflage. You don’t have to be louder to be seen; you have to be clearer. Keaton never sought the spotlight—she controlled its wattage. She defined womanhood with a levity and youthfulness in her dressing like no one else could.

At PROVOKED, we talk a lot about agency. Keaton modeled it without slogan or sermon. She dressed for work—inside and out—not applause. She declined the criticism of consensus and the male gaze with indifference. A hat tipped just so. A jacket cut to argue. A radiant smile, and self-mocking love of life.

The message: I am not an invitation; I am a decision already made.

Eccentricity as Method

Eccentricity, for her, was method, not mood. Pattern pileups, oversized frames, playful gloves. Not asking “too much,” but “what if?” She treated the closet like a lab: edit, revise, repeat. Even her “comfort clothes” were statements. She wore what she loved and what would last—practicality even became rebellion. Take wide-leg pants, for example. They can feel like permission, the body given room to think. And that’s liberation. When she walked the carpet in a striped suit or heavy boots, it was like wearing utility with wit.

Her peers praised the humor and refusal to conform that defined her. Keaton modeled a disciplined way of thinking that was wholly her own. Even her thrifting had theory. A $12 pair of jeans wasn’t nostalgia; it was anthropology, proof of a life lived in drafts. Consistency, often mistaken for stagnation, was her mastery: refine, don’t reinvent.

She didn’t negotiate with time.

She distilled.

The Mirror Test

If this reads like fashion talk, look again. The closet is often the first place a woman makes unilateral decisions. To design it rather than surrender to it is training in autonomy. So what do we do with a legacy like hers?

Apply it.

Tomorrow morning, approach the mirror with curiosity, not compliance. Wear the turtleneck you keep saving. “Buy one. I dare you. Give one a try” she wrote in her 2014 memoir Let’s Just Say It Wasn’t Pretty.

Replace “Does this make me look…?” with “Does this let me think?”
You don’t need to be louder, only legible to yourself. That’s the Keaton test. If what you wear lets you move, decide, and decline without explanation, you’ve passed.

In PROVOKED’s world—restless, skeptical, insistent—Diane Keaton becomes more than an idol. She becomes a primer for possibility.

Wear what endures. Wear what makes you delight in a giggle.

Keep humor visible and apology out of frame.

And when you meet your mirror, skip permission.

About the Author

Susan Dabbar has built a career on reinvention, creativity, and strategic vision, launching and leading businesses across four decades in industries as varied as they are rewarding. Now, as the Founder and Editor-in-Chief of PROVOKEDmagazine, she’s channeling that same energy into a media platform that questions and redefines the conversation around autonomy, ambition, and agency for women.

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