Diane Keaton was not just a style icon—she was a revolutionary figure in celebrity fashion. Her distinctive, often eccentric style was not dictated by the fleeting whims of Hollywood trends or the pressures of celebrity image-making. Rather, she embodied a vision of personal style that defied conventional standards and remained uniquely her own. With her signature look of tailored trousers, menswear-inspired shirts, wide-brimmed hats, and oversized glasses, Keaton proved that style could be far more than just about clothes—it could be a form of self-expression, wit, and intelligence. In many ways, her style was as much an act of subversion as it was an embrace of personal freedom.
The Evolution of Diane Keaton’s Iconic Wardrobe
Diane Keaton’s personal style has always been about authenticity. It was never about fitting into the mold of what a glamorous movie star was supposed to look like. In fact, one could argue that Keaton was an antithesis to the Hollywood beauty ideal. While she was undeniably stunning—renowned for her bone structure and sharp features—she never led with her looks. Instead, she chose to dress for herself, often blurring the lines between masculine and feminine attire, and in doing so, completely redefined what it meant to be a female style icon in Hollywood.
Her fashion was not about appearing seductive or relying on the stereotypical markers of femininity—tight dresses, high heels, and low-cut tops. Instead, Keaton opted for what was, in her own words, a “borrowed-from-the-boys” aesthetic, which took on a life of its own. Her wardrobe became synonymous with tailored jackets, button-down shirts, waistcoats, and a variety of trousers, all styled with an ease and grace that transcended the ordinary. This blend of elegance and quirkiness created a look that was impossible to ignore but difficult to define. It was part Beau Brummell (the 19th-century style icon famous for bringing tailoring into fashion), part Charlie Chaplin (the beloved silent film comedian known for his oversized suit and distinctive gestures), and yet it was unmistakably Keaton.
“Annie Hall” and the Birth of Her Signature Look
Keaton’s role in Annie Hall (1977) is, without question, a seminal moment in the history of fashion in cinema. But what many might not know is that much of her character’s wardrobe was simply pulled from her own closet. Keaton was so invested in making her character feel authentic that she layered her personal pieces—items she had already worn in her daily life—into her onscreen costumes. Woody Allen, the film’s director, allowed her this freedom, even stepping in when the costume department suggested more traditional attire. “Leave her. She’s a genius. Let her wear what she wants,” Allen famously said, acknowledging Keaton’s unparalleled ability to infuse herself into her character’s wardrobe.
In many ways, Annie Hall’s iconic look—wide-legged trousers, oversized blazers, button-down shirts, and neckties—was simply a reflection of Keaton’s own personal style. While many credit designer Ralph Lauren with dressing Keaton for her Oscar-winning role, the actress herself was quick to clarify in her 2024 book Fashion First that Annie’s style was Diane’s style. The line between the character and the woman who portrayed her was beautifully blurred.
Keaton’s style was also more than just about clothes; it was about the way she wore them. Her use of kinesics, or body language, was central to her style. She understood that clothing could serve as a tool for self-expression, accentuating her every gesture. The tip of a hat, the hand placed casually in a pocket, or a slight tilt of the head all became part of her broader, almost performative, style language. Her physicality was just as important as the clothes themselves.
Personal Style vs. Hollywood’s Expectations
Diane Keaton’s career was shaped by her resistance to the expectations Hollywood tried to place upon her. During the 1970s and 1980s, when female stars were often confined to a narrow set of gendered sartorial codes, Keaton’s unconventional approach was groundbreaking. In a time when many actresses were expected to wear body-hugging gowns and glamorous dresses, she chose to wear trousers, hats, and jackets in a manner that celebrated comfort, intellect, and individuality.
Throughout her career, Keaton’s fashion choices often caused a stir, yet she stayed true to herself. When other actresses were opting for high heels and figure-hugging dresses at major events, Keaton showed up in flat shoes and loose silhouettes, demonstrating a level of comfort and confidence that others may have seen as unfashionable at the time. In fact, Keaton was often ridiculed for her choices, from white socks with sandals to wearing tartan shirts on the red carpet. Yet, her refusal to conform was exactly what made her so remarkable. She showed that style doesn’t have to adhere to traditional standards to be chic.
One of Keaton’s most memorable red-carpet moments came in 2004, when she wore a tailcoat with a white carnation and black leather gloves to the Oscars, once again breaking the rules of Hollywood glamour. The look was uniquely hers: formal yet playful, masculine yet undeniably feminine in its execution.
Keaton’s decision to break away from Hollywood’s restrictive fashion codes did not end with the 1970s. As she matured, her style grew more playful and eccentric, but always remained grounded in the personal choices she made about what to wear. In 2023, for instance, Keaton showed up to a Thom Browne fashion show in Paris wearing a pinstripe seersucker suit, platform two-tone brogues, and carrying a sausage dog-shaped basket. The look was quintessential Keaton—unexpected, whimsical, and completely in line with her unique fashion sensibility.
Diane Keaton’s Enduring Influence on Fashion
Though Keaton’s fashion choices may have once been seen as rebellious, her legacy has paved the way for a broader conversation about the importance of personal style in the fashion industry. Today, many celebrities and influencers champion gender fluidity in fashion, embracing menswear-inspired looks in a way that feels fresh and exciting. Keaton’s work in the 1970s and beyond can be seen as a precursor to this shift in fashion, where clothing becomes a tool for self-expression rather than merely a means to fit into a mold.
Her influence extends beyond film, too. Designers have long cited Keaton as a muse, with many praising her ability to make tailoring look effortless and playful. In fact, her look has been emulated by numerous fashion icons who appreciate the freedom that comes with unconventional dressing. For Keaton, her wardrobe was a way of pushing boundaries, making a statement, and embracing who she was without compromise.
A Life Lived Beyond the Machine
Diane Keaton was never interested in being a product of the Hollywood machine. While she undoubtedly became a star, her approach to fashion—and her life as a whole—was about individuality and self-determination. In a world where women were often pressured to conform to a certain image, Keaton’s style was a quiet rebellion. It was a rebellion against the narrow definitions of beauty, glamour, and success. She dodged the stamp of the machine, creating a space where she could simply be herself—and in doing so, she became one of the most influential style icons of all time.
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