
Remembering Diane Keaton: A Timeless Icon Beyond Trends
von Eva Winterer
Remembering Diane Keaton: A Timeless Icon Beyond Trends
How Diane Keaton's Annie Hall Style Revolutionized Fashion and Built a Lasting Brand Legacy.
von Eva Winterer
The fashion, film, and cultural worlds mourn the death of Diane Keaton, who passed away on October 11, 2025, at the age of 79. In an industry often dictated by fleeting trends and red-carpet mandates, Keaton charted her own course, blending eccentricity with elegance in a style that was profoundly personal. Her sartorial influence cannot be separated from her multifaceted career in acting, directing, and writing, her political engagement, and her unwavering commitment to personal independence. Keaton didn't just wear clothes—she demonstrated that fashion is an extension of one's identity.
A Style Without Compromise
Keaton never chased trends. Born in 1946 in Los Angeles, she cultivated a look that was entirely her own: wide-leg trousers, oversized hats, layered neutrals, and bold accessories that mixed masculine tailoring with feminine elements. As she noted in a 2023 Instagram video, "Annie Hall was the beginning—the beginning of my response to wearing whatever the hell I liked." That film, Woody Allen's 1977 masterpiece, catapulted her to stardom and immortalized her aesthetic: the menswear-inspired ensembles, complete with ties, vests, and bowler hats, became cultural shorthand for liberated femininity.
The turning point was precisely that 1977 film. The title character's look—wide trousers, vests, ties, and hats—quickly became a global phenomenon. Crucially, this style wasn't created by the costume department; it was Keaton's own. Both director Woody Allen and designer Ralph Lauren confirmed this. Allen instructed costume designer Ruth Morley to give Keaton free rein: "She's a genius. Let her do what she wants, let her wear whatever she likes." Lauren wrote in the foreword to Keaton's book Fashion First: "Annie's style was Diane's style."
Keaton described the inspiration for her outfits as coming directly from the urban environment: "My muses were the women of New York City, walking through the streets of Soho in wide pants and blazers." The immediate market impact was enormous. By summer 1977, the New York Times documented, with photos by Bill Cunningham, how the "Annie Hall look" conquered the streetscape. Keaton demonstrated that personal style can have immense commercial and cultural impact, functioning independently of top-down trend cycles.
Unlike her Hollywood peers who followed seasonal dictates, Keaton rejected conformity. She wore pants to awards ceremonies, neon hues for errands, and Thom Browne jackets with skirts layered over trousers because, as she put it, "I'm insane." Her aesthetic—neutral tones, textured fabrics, and dramatic silhouettes—felt both classic and edgy, minimal yet bold. Fashion commentators like Anne Fontaine celebrate her as a "rare breed," one who politicized fashion by challenging gendered norms. In her book Fashion First, Keaton reflects on her scrapbooks of clippings, from early Goodwill finds to red-carpet experiments, admitting missteps with self-deprecating humor: "You can tell that's more like me—it's all sloppy."
Her aesthetic remained remarkably consistent over the decades. Core elements included suits, turtlenecks, wide belts, and hats, mostly in a black-and-white color palette. This uniform was a personal trademark and expression of a clear position. She wore pants to formal award ceremonies and bowler hats to galas—conscious rejections of standardized red-carpet culture. As she told WWD, she simply wore what she liked.
This authenticity resonated globally. A recent NZZ Bellevue piece praised her as a style role model for every generation, noting how her "Annie Hall" look—bundled trousers, crumpled shirts, and round glasses—encouraged personal aesthetic discovery over algorithmic body typing or color seasons. Keaton's influence endures in contemporary designers like The Row and Phoebe Philo, who echo her understated rebellion. Her legacy? Proving that style isn't trend-driven—it's personality made visible.
From Personal Style to Brand Power
This clear brand identity enabled Keaton to transfer her aesthetic vision to other business fields. She developed a 109-piece collection for interior brand Hudson Grace, a fabric line with Fabricut Inc., and a lighting collection with Aidan Gray. Her rationale for focusing on black and white in her Hudson Grace collaboration exemplifies her pragmatic design philosophy: "It's clean, simple, and, if you ask me, it never goes out of style."
Diane Keaton's legacy is thus more than a collection of iconic outfits. She provided proof that an uncompromisingly personal vision can form a powerful and economically viable brand. By resisting industry pressure, she became an influential force herself, inspiring consumers and designers like Ralph Lauren and Thom Browne, redefining Hollywood style.
Artist and Author
While fashion was Keaton's signature, her career extended far beyond it. Her acting prowess earned her an Oscar for Annie Hall and iconic roles in The Godfather trilogy, Reds, and Something's Gotta Give. She directed films like Heaven (1987) and documentaries, often exploring themes of family, aging, and female autonomy. As an author, Keaton penned memoirs such as Then Again (2011) and Brother & Sister (2020), examining her upbringing in a creative California household and complex family dynamics. Her photography books, like House (2012), revealed a passion for architecture and preservation, showcasing overlooked beauty in abandoned structures.
Keaton's personal life added layers to her public persona. Never married, she adopted two children, Dexter and Duke, in her 50s, championing single motherhood and redefining family norms. Her high-profile relationships—with Woody Allen, Warren Beatty, and Al Pacino—fueled tabloid interest, but Keaton maintained fierce privacy, often using humor to deflect scrutiny. In interviews, she spoke candidly about aging gracefully, rejecting Hollywood's youth obsession: "I'm not going to be 20 again, and that's okay."
Political Engagement and Social Advocacy
Politically, Keaton wasn't a vocal activist, but her influence was quietly significant, woven into her work and public statements. A lifelong Democrat, she voiced opposition to the Iraq War in the early 2000s and supported environmental causes, aligning with figures like Jane Fonda in climate advocacy. Her role in Reds (1981), portraying journalist Louise Bryant amid revolutionary fervor, reflected her interest in social justice. Keaton challenged patriarchy through her art—Annie Hall's style was a feminist statement, subverting gender expectations long before it became mainstream discourse.
In later years, she engaged with cultural politics, critiquing ageism in Hollywood and promoting women's stories. Her 2014 book Let's Just Say It Wasn't Pretty tackled beauty standards with wit, advocating for self-acceptance over surgical enhancements. Keaton also supported LGBTQ+ rights, drawing from her experiences in inclusive artistic circles. While not overtly partisan, her life embodied progressive values: independence, creativity, and resistance to conformity.
A Lasting Impact
Diane Keaton's death leaves a void, but her legacy endures as a blueprint for living authentically. In fashion, she taught us that style is self-expression, not submission to trends—a lesson immortalized in her video "An Obsession with Style," where she flips through scrapbooks with infectious joy, declaring fashion "everything." Beyond that, her career as an artist and advocate demonstrates the power of multifaceted lives. She was a style icon, yes, but also a trailblazer who normalized eccentricity, championed personal freedom, and subtly shaped cultural conversations.
As high-end publications reflect on icons, Keaton stands out for her holistic impact. Designers might recreate her looks—oversized hats, chunky belts, full skirts—but her true gift was permission: to be authentic, to evolve without apology. In a world of fast fashion and fleeting fame, Diane Keaton was timeless. Rest in style.