Diane Keaton’s Singular Style: Audacious, Gutsy and Independent

She was the ultimate cool girl who defined menswear-influenced style in the 1970s, and almost a half-century later Diane Keaton remained the ultimate cool woman both onscreen and off, making style statements in films and on red carpets that were equal parts uncommon, fun and age-appropriate, and which always felt wholly authentic to her personality.

Keaton, who passed away on October 11 at the age of 79, was already a star before 1977’s Annie Hall, with roles that included 1972’s The Godfather and its 1974 sequel, as well as Woody Allen films like 1972’s Play It Again, Sam (after starring in Allen’s Broadway play by the same name) and 1973’s Sleeper. But it was Annie Hall that vaulted Keaton into dual stratospheres of acting and style, winning a best actress Oscar for the titular role of the free-spirited woman fond of tossing off a phrase like “la-di-da,” though it’s easy to make the case that her fashion in that film made a larger contribution to her legacy. The androgynous Annie Hall look, a layering of menswear-inspired pieces that felt artful yet unplanned, not only became an essential fashion trend of the late 1970s, it also continues to be referenced in collections to this day.

Keaton’s contributions to her look in Annie Hall caused a conflict with the film’s costume designer, Ruth Morley, who initially envisioned a character who wasn’t so fully formed from a style perspective. Having written both the character and the film based on Keaton and his relationship with her in the late 1960s through early ’70s, Allen intervened and asked Morley to let Keaton control her own onscreen style during filming; the resulting wardrobe blended pieces from vintage stores and Keaton’s own closet, as well as separates contributed by Ralph Lauren.

In the summer following the film’s release in April 1977, The New York Times highlighted the trend — “the Annie Hall look is now popping up on the streets with amazing frequency,” it proclaimed — and included an interview with Morley. “The look was designed for a girl who didn’t quite know who she was,” said Morley, who died in 1991. “The girl is little confused but not a hippy; she’s unusual, she’s trying to find herself … [b]ut even though she didn’t yet know who she was, she had originality and she was creative.”

That last quote also might apply to Keaton overall, with one exception: she knew exactly who she was, and throughout her life she often made that statement via what she wore. The actress-director-producer’s signature style resulted in a 2024 book, Diane Keaton: Fashion First (Rizzoli, $55), in which Keaton credits her mother as her style inspiration. Her parents’ names? Jack and Dorothy Hall. “She was dolled up no matter what,” Keaton wrote of her mother. “And I was following right behind her, loving every minute of it.”

Lauren penned the book’s foreword, noting that Keaton attended his fashion shows long before she became famous. “I am often credited with dressing Diane in her Oscar-winning role as Annie Hall. Not so,” he wrote. “Annie’s style was Diane’s style. Very eclectic. She loved floppy hats and oversized men’s jackets. She loved dangly neckties and layers of sweaters and vests and cowboy boots. Around the same time, I sent models down the runway dressed like that. We shared a sensibility, but she had a style that was all her own.” 

Soon after Keaton’s death was announced, Lauren posted a statement to his brand’s social media: “Diane always marched to the beat of her own drum — in the way she lived, the way she saw the world, and the way she made all of us feel,” he said. “She was authentic, unique and full of heart. She was always herself—one of a kind.”

It wasn’t difficult to see Keaton’s personal style in her onscreen looks. The details are all there, from menswear inspirations revealed through tailored trousers and jackets, the latter often cinched with a wide belt, to an appreciation for accessories, hats in particular. She added that self-identity to her character’s corporate look in 1987’s Baby Boom and to the polished, tailored pieces she wore in 1990’s The Godfather Part III (though admittedly Milena Canonero’s costumes struck many film and fashion critics as being somewhat anachronistic, feeling more current than the film’s time period of late 1970s/early 1980s).

More recently, Keaton’s roles also became an inspiration for women who desired to feel stylish and confident when they were no longer in their 20s and 30s, especially as fashion historically has eschewed older demographics in favor of youth. Tailoring was key to her character in films like 1996’s The First Wives Club, while in 2003’s Something’s Gotta Give, a white turtleneck — another offscreen favorite piece — not only helped define her character, it also became a plot point, with Jack Nicholson cutting the sweater off her as a bit of comedic foreplay in their climactic love scene. In 2014’s 5 Flights Up, Keaton is both adorable and stylish as the wife of Morgan Freeman in this story of an older couple who must navigate decisions and the next phase of their life while selling their walk-up apartment in Brooklyn. Via an effortless blend of sweaters, tailored jackets, scarves and a kicky beret, Keaton’s look might have become style goals for women decades her junior.

Keaton expressed her personal style most fully on red carpets, and she was unafraid to have fun with it — indeed, “quirky” was an adjective style pundits employed to describe some of her event looks. When a jacket was paired with a skirt, either slim and pencil-shaped or bursting in ballerina tulle, it was always belted and worn with statement shoes. Bowler hats and berets were essential accessories, and she often wore gloves, a detail also included in the wedding scene of 1991’s Father of the Bride. Ralph Lauren remained a favorite designer, including a Charlie Chaplin-inspired suit he created for her to wear at the 2004 Academy Awards, when she was nominated for best actress for Something’s Gotta Give, and a velvet tuxedo Keaton wore to the 2014 Golden Globe Awards, when she accepted the Cecil B. DeMille Award for Allen, who famously has avoided awards ceremonies throughout his career.

When Keaton won the best actress Oscar for Annie Hall at the 1978 Academy Awards, she wore a look by Giorgio Armani. Today Armani is considered a mainstay of awards-show style, but his look for Keaton, a tan double-breasted jacket layered over a striped ankle-length skirt, was the first time the legendary Italian designer had dressed a star for the red carpet. In 2020, Armani noted in an interview with Grazia that Keaton “had a completely different idea of what the image of stardom should be — she wanted to be a relatable person first, a star second,” he said. “You can see how Diane makes a tailored jacket — in a style normally associated with a man’s suit — look thoroughly modern and individual.” In a 2021 Instagram post, the house of Armani also noted that the designer, who died in September 2025, contributed to the costumes Keaton wore in Father of the Bride.

While Lauren remained a favorite, in recent years Keaton also exhibited a preference for Thom Browne, whose slim and forward-thinking menswear aesthetic likewise seemed tailor-made for the actress. Last September she chose a striped Thom Browne suit for the announcement of an eyewear collaboration she was doing with Connecticut-based Look Optic — because Keaton’s glasses, like her waist-cinching belts, tailored jackets and bowler hats, also were integral to her signature style.

Some may wonder whether the injection of Keaton’s personal taste into her character’s costumes ever might have felt inauthentic, when actually the opposite is true, for one key reason: She primarily played women who either exuded strength throughout their stories or, in the case of films like Baby Boom or Something’s Gotta Give or The First Wives Club, they found their strength and confidence over the course of that journey. They might not have said “la-di-da,” but each found her inner Annie Hall by the time the credits rolled, and in doing so became inspirations, in both style and sensibilities, for women of every age.