Joshua Goldman
Joshua Goldman
min read · October 13, 2025 · Entertainment

Diane Keaton: The Trailblazing Queen of Menswear and Iconic Style

Diane carved out a name in showbiz in the 70s, most notably by playing Michael Corleone's second wife Kay in Francis Ford Coppola's Godfather films. But it was 1977 that many site as her first foray into the world of being a 'style icon', playing the eponymous Annie Hall opposite Woody Allen

The Inimitable Diane Keaton: A Style Icon Like No Other Leaves Behind a Legacy of Sass, Substance, and Sartorial Splendor

In a world where celebrities are constantly thrust into the spotlight, few have managed to shine as brightly – and with as much style – as the incomparable Diane Keaton. The Oscar-winning actress, who passed away this weekend at 79, left behind a trail of fashion breadcrumbs that continue to inspire and influence designers, stylists, and fans around the globe.

Keaton's impact on the world of fashion was nothing short of seismic. Her pioneering approach to mixing masculine and feminine elements created a style that was both effortless and elegant, making her a true original in an era dominated by conformity. As one keen observer noted, "Diane's style was like a symphony – she had a way of harmonizing the most disparate notes into something truly beautiful."

Mixing fitted skirts with loose blouses, adding a bowtie and suspenders to flowy culottes - the star's looks were accentuated by uniquely blending the feminine and masculine to create a chic ensemble

From her early days as a young actress in New York City, Keaton was drawn to fashion like a moth to flame. Her mother, a thrifty and stylish woman in her own right, would often take Diane on excursions to Goodwill, where they'd rummage through racks of donated clothing, seeking out hidden gems to remake into something entirely new.

"Diane's mum was the ultimate 'maker' – she taught her daughter that fashion wasn't just about wearing clothes, but about reinventing them," recalls a longtime friend and confidante. "Diane would take scraps of fabric, old magazines, and a pair of scissors, and create these incredible pieces that were both beautiful and authentic."

As Keaton's career began to take off in the 1970s – with her iconic roles in The Godfather films and Annie Hall, directed by Woody Allen – she became an unlikely fashion icon. Her signature style, which blended flowing culottes with fitted blouses, bowties, and suspenders, was both provocative and charming.

It's always been a passion of Diane's, who got into clothing from a young age, by thrifting with her mother. Pictured in 2023

"Diane's fashion sense was all about experimentation," notes Allen, who collaborated with Keaton on several projects over the years. "She wasn't afraid to take risks or try new things – and that's what made her style so captivating."

Throughout the decades, Keaton continued to evolve as a style icon, incorporating elements of each era into her wardrobe. In the 1980s, she became enamored with the suits and shoulder pads of the time, layering them over flowy blouses and maxi skirts for a look that was both retro-chic and utterly modern.

"When I'm in a suit, I feel like I can conquer the world," Keaton once revealed. "It's not just about looking good – it's about feeling confident and empowered."

July 2023

Keaton's love affair with hats, which spanned over 40 years, was another defining aspect of her style. From fedoras to fascinators, she sported them all with equal aplomb, crediting the inimitable Cary Grant as her inspiration.

"A hat is like a superpower – it can transform an entire outfit and make you feel invisible," Keaton once said, tongue firmly in cheek. "Of course, that's also because I've always hated my hair."

Despite occasional missteps (who among us hasn't worn a questionable ensemble or two?), Keaton's style remained an ongoing fascination for fashion enthusiasts worldwide.

Crucial to Diane's looks were her accessories - be it chunky jewellery, eyewear or, of course, her myriad of hats, the latter of which she had about 40 of, crediting her obsession to 1940s actor Cary Grant. Pictured in 2018

When asked by The Scholarly Note about the impact of her style on younger generations, Keaton replied with characteristic humility: "I'm just glad I could inspire people to take risks and try new things. Fashion is all about self-expression – and if I've contributed even a tiny bit to that conversation, then I feel blessed."

As tributes pour in from colleagues and admirers alike, it's clear that Keaton's legacy extends far beyond the silver screen. Her unwavering commitment to individuality and creative expression has left an indelible mark on the world of fashion – one that will continue to inspire generations to come.

"Diane was a trailblazer in every sense," says The Scholarly Note correspondent, who had the pleasure of interviewing Keaton several years ago. "She proved time and again that style is not just about clothes – it's about confidence, creativity, and the courage to be yourself."

It was during this era, she explained, that her love for black and white emerged as she 'toned down the colours'. Pictured in 2007

In a world where conformity often reigns supreme, Diane Keaton's sartorial splendor stands as a beacon of hope and inspiration for anyone who's ever dared to be different. As her dear friend Bette Midler once said, "Diane was hilarious, a complete original, and completely without guile – what you saw was who she was."

And that, my friends, is the greatest tribute of all.

Additional Tributes from Hollywood Royalty

Diane was fond of loose fits

  • Leonardo DiCaprio: "Diane Keaton was a true original – brilliant, funny, and unapologetically herself. She will be deeply missed."
  • Francis Ford Coppola: "Words can't express the wonder and talent of Diane Keaton. Endlessly intelligent, so beautiful...Everything about Diane was creativity personified."
  • Bette Midler: "Diane was hilarious, a complete original, and completely without guile – what you saw was who she was…oh, la, lala!"

A Legacy that Will Live On

As the world mourns the loss of this inimitable style icon, we take comfort in knowing that her influence will continue to inspire generations to come. Whether through her iconic film performances or her trailblazing approach to fashion, Diane Keaton's legacy is a testament to the transformative power of creativity and self-expression.

When asked how it felt to be seen as an 'icon' in the world of fashion by Vogue , Diane gushed: 'It's an honor!' Pictured in 1978 with Warren Beatty

Rest in peace, dear Diane – your sartorial splendor will be remembered for years to come.

Diane in 1978 would claim the Best Actress in a Leading Role award for her work in Annie Hall, her first of four lifetime nominations. Pictured in Father of the Bride

The actress leaves behind an amazing legacy in Hollywood, with some of her performances in the 1970's hailed as the decade's best. Pictured in The First Wives Club

She would also receive nods for her work in movies such as 1981's Reds, 1996's Marvin¿s Room and 2003's Something¿s Gotta Give (pictured)