Personal style is as unique as a fingerprint, and few have exemplified this concept as beautifully as Diane Keaton. Known for her iconic blend of button-up shirts, ties, snappy waistcoats, and baggy trousers, her fashion choices present a quirky, yet sophisticated nod to menswear. This distinctive style is a delightful mix of classic elegance and playful eccentricity—part Beau Brummell and part Charlie Chaplin—showcasing how truly personal style can be both unique and endearing.
What sets Keaton apart is that her charm emanates from the fact that her wardrobe was authentically hers. In an era of Hollywood where cookie-cutter looks prevailed, she stood out as a quietly subversive force, consciously opting for individuality over mainstream allure. Rather than leading with her beauty, she emphasized her intellectual appeal—her sunny smile and endearing quirks signal a persona unlike any other. This refusal to conform made her a beacon of authenticity in an often homogenous celebrity landscape.
Reflecting on her most famous role, Keaton once noted, “I look back on Annie Hall and can’t talk about that movie without talking about the fashion. It was everything to me. I loved being able to dress like myself.” This sentiment encapsulates how deeply intertwined her character’s wardrobe was with her personal style. Much of what audiences saw in the film was indeed drawn from Keaton’s closet, creatively layered with thrift shop finds she adored. Her collaboration with Woody Allen proved essential; when costume designers suggested alternative styles, he insisted, “Leave her. She’s a genius. Let her wear what she wants.”
Interestingly, the fashion world often attempted to credit the legendary Ralph Lauren as the architect behind Keaton’s distinctive look in Annie Hall. However, Lauren himself acknowledged in his foreword to her 2024 book, Fashion First, “I am often credited with dressing Diane in her Oscar-winning role as Annie Hall. Not so. Annie’s style was Diane’s style.” This homage speaks volumes about how fashion, like cinema, can blur the lines between creator and inspiration.
Keaton’s ability to bring life to tailored silhouettes captured the spirit of understated glamour. Much like Cary Grant, her sharp outfits—a mix of structured jackets, belted trousers, and quirky ensemble accessories like hats and glasses—came alive with her animated presence. Furthermore, echoes of Fred Astaire’s elegant fluidity can be felt in her wardrobe choices, each nuance pointing to her understanding of physical comedy, as she employed clothing as an extension of her expressive style, accentuating her gestures as easily as she donned a scarf or tipped her hat.
At times, Keaton’s unique sartorial choices attracted criticism—think tartan shirts on award show red carpets or her daring Oscar ensemble featuring a tailcoat paired with a white carnation and black leather gloves in 2004. Her penchant for the unexpected shone through at a Thom Browne fashion show in Paris in 2023, where she sported a pinstripe seersucker suit complete with playful platform two-tone brogues and a basket shaped like a sausage dog. Yet, despite the flak she received, her confidence in her identity remained unshaken.
In her book, Fashion First, Keaton expands on the idea that wearing men’s clothing afforded her a sense of privacy amid the glaring Hollywood spotlight. As she describes, a big belted coat is her version of a ballgown—a notion that sheds light on her deep understanding of silhouette and the psychology behind clothing choices. This “brainy elegance” not only helped popularize masculine styling in women’s fashion but also allowed Keaton to redefine the aesthetic landscape for women in media. Although she disclaims that she pioneered this trend, noting inspiration came from “the cool-looking women” in SoHo at the time, her original approach solidified her status as a true icon—one who didn’t just wear a style but invented it.
Many fans have encountered the magic of Keaton in person. One such encounter at a Ralph Lauren party in Los Angeles left a lasting impression. Starstruck, the admirer nervously requested a photo, only to be met with Keaton’s warm response: “Sure! Let’s take a selfie,” she insisted, leaning in close with her trademark beaming smile, that warm glow she naturally exuded. Clad in a high-collared white blouse and bowler hat, she looked every bit the icon that she is, effortlessly blending warmth and style.
Keaton’s style is much more than a collection of clothes; it’s a celebration of individuality, a testament to the power of self-expression. While the typical narrative of Hollywood glosses over character in favor of appearance, Diane Keaton stands as a vibrant contradiction, proving that true style is often found in authenticity. She remains, and perhaps always will be, an everlasting inspiration to those who dare to embrace their unique selves.
For more, read 10 ways to master Diane Keaton’s style