The passing of Diane Keaton at 79 prompted an outpouring of tributes, not just for her charming and potent on-screen performances, but for a singular achievement in fashion: she lived personal style. From her peers like Bette Midler and Goldie Hawn to millions of fans who connected with her in Annie Hall or even the recent Justin Bieber “Ghost” music video, the resounding chorus celebrated her sartorial courage. Keaton’s signature was a defiant rejection of Hollywood’s fashion expectations, built upon trousers, blazers, and eccentric accessories—bowler hats, chunky belts, and men’s ties—all chosen for the sheer, unadulterated joy of self-expression. She never bowed to stylist traditions or designer demands, preferring to curate her own wardrobe from labels like Richard Tyler, Ralph Lauren, and Comme des Garçons, making every garment “totally her own.” Her legacy is a lesson in authenticity, proving that true style is an unfiltered expression of self, enduring long after the curtain falls.
Rejecting the Gown: The Annie Hall Revolution
Diane Keaton’s most definitive statement on style was delivered not on a street corner, but on the most glamorous stage in Hollywood: the Oscars. Her appearance solidified her as a fashion iconoclast.
When Keaton accepted her Best Actress Oscar for Annie Hall in 1978, she famously eschewed the traditional opulent designer gown. Instead, her look was an almost confrontational blend of menswear and vintage sensibility: a gray blazer, a white button-down shirt, a striped calf-length skirt worn over trousers tucked into boots, and an infinity scarf. This was an era before stylists became mandatory, but Keaton chose to continue selecting her own looks for her entire career, often wearing labels she personally adored, such as Richard Tyler, Ralph Lauren, and Giorgio Armani. She refused to adopt the default movie-star uniform, choosing comfort, eccentricity, and character over conventional red-carpet sex appeal. The act of wearing a simple carnation brooch and almost no jewelry while accepting the industry’s highest honor was, in itself, a powerful, quiet rebellion.
The Cinematic Style: From Tomboy Chic to Power Broker
While Annie Hall is often cited as Keaton’s peak style moment—a character dressed in a delightful mash-up of her own vintage finds, vests, and ties—her on-screen wardrobe was consistently used to convey character depth and professional competence.
In the 1987 film Baby Boom, Keaton played J.C. Wyatt, a workaholic investment broker who suddenly inherits an infant. Her 1980s work wardrobe was a masterclass in comfortable, yet sharp, professional dressing. This included belted skirt suits with pronounced shoulders, silk ascots, and patent black pumps. This style resonated deeply with professional women of the time, providing a template for non-revealing, slightly tomboyish silhouettes that sacrificed neither elegance nor glamour for practicality. Whether playing the supportive mom in Father of the Bride or leading the charge in The First Wives Club—where her hip-swinging, head-bobbing finale in a cool white skirt suit became an iconic moment of liberation—Keaton’s clothing always served the woman wearing it, reinforcing her character’s strength and spirit.
The Literary Legacy of Sartorial Obsession
Keaton’s commitment to personal style was so profound that she dedicated an entire book to the subject, providing a rare, intimate look into the source of her sartorial joy and obsession.
Last year, Rizzoli published “Fashion First,” a book written by Keaton herself that charts her personal journey through clothes and memories. In it, she details formative experiences, such as her early desire to wear a bowler hat to her prom, her ongoing obsession with accessories, and the stylistic influence of icons like Cary Grant. This narrative solidifies that her style was not a reaction to trends, but a deep-seated, lifelong passion. In the book’s foreword, designer Ralph Lauren perfectly summed up her gift: “Diane has worn my clothes many times but she’s always made them totally her own.” This is the pure definition of personal style—a creative license to interpret and own fashion, irrespective of the designer’s original intent.
The Digital Renaissance: Post-Age Avant-Garde
Even in her later years, long after her most iconic film roles, Diane Keaton utilized social media to continue her exploration of style, offering a fresh, unapologetic vision of post-age fashion.
Beginning in 2019, Keaton became an unlikely yet beloved figure on Instagram, using outfit mirror selfies to document her latest stylistic pursuits. Her late-era look often leaned into a mostly black-and-white palette, incorporating graphic elements like check print or houndstooth, frequently with an air of Japanese avant-garde sensibility reminiscent of designers like Comme des Garçons or Yohji Yamamoto. She layered on accessories, including her favorite piled-on cross necklaces, treating her daily dressing as a personal form of performance art. This continued expression, seemingly done “not for attention or likes but because it made her feel alive,” resonated powerfully with her fans. As her peer Bette Midler noted in a tribute, “What you saw was who she was… oh, la lala!”—a powerful statement that her deliberate, covered-up yet expressive style always revealed the authentic woman beneath.
