Personal style is the best kind of style there is, and no one did personal style better than Diane Keaton. Her signature look was shirts and ties, snappy waistcoats and baggy trousers, an idiosyncratic version of menswear that was somehow both elegant and goofy. It was part Beau Brummell and part Charlie Chaplin. “Borrowed from the boys” does not do it justice; she made it entirely her own.
The charm of her wardrobe was that it was exactly her. She was a world-class beauty who didn’t lead with her looks. A quiet subversive who, in the most cookie-cutter of Hollywood eras, dodged the stamp of the machine and chose to live her life her own way. It was never about menswear as power dressing. With a sunny smile, she broke all the rules of celebrity dressing with the disarming sweetness and quiet intelligence that she brought to her screen personas.
“I look back on Annie Hall and can’t talk about that movie without talking about the fashion,” she once said about her most memorable role. “It was everything to me. I loved being able to dress like myself.”
Much of Keaton’s on-screen wardrobe as Annie Hall was, simply, Keaton’s own wardrobe. She layered what she already had with pieces she bought herself from thrift stores. When the costume department tried to steer her in a different direction, Woody Allen intervened, telling them: “Leave her. She’s a genius. Let her wear what she wants.”
Naturally, the Hollywood patriarchy did its best to hand the laurels to a man, Ralph Lauren, who supplied a blazer and a tie for Keaton to wear as Annie Hall. But Lauren wrote, in the foreword to Keaton’s 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.”
Like Cary Grant, Keaton had a way of breathing life into a tailored silhouette. She made heavily structured outfits – jackets, belted trousers, chunky shoes, the omnipresent banded hats and spectacles – feel alive. There are echoes, too, of Fred Astaire’s kinetic elegance in Keaton’s wardrobe. A gifted physical comic, she used the way she wore clothes – the tip of a hat, the hand stuffed in a pocket – to accentuate her gestures.
Her more eccentric choices – tartan shirts on the red carpet, white socks with evening sandals – brought her a fair amount of media flak over the years. A tailcoat with white carnation and black leather gloves at the Oscars in 2004. A pinstripe seersucker suit with platform two-tone brogues and a basket in the shape of a sausage dog at a Thom Browne fashion show in Paris in 2023. But she stuck to her guns.
In Fashion First, she writes that wearing men’s clothing gave her privacy. A big belted coat, she says, is her version of a ballgown. (Like all great dressers, she had an instinctive appreciation of the importance of a silhouette.) Her screwball, brainy elegance helped bring masculine styling into the mainstream of women’s fashion. Although she demurred the notion that she came up with it – she once said the inspiration for Annie Hall came in part from what “the cool-looking women” in New York’s SoHo were wearing at the time – she was a true original. She didn’t just wear a style, she invented a style.
I saw Keaton once, a few years ago, at a Ralph Lauren party in Los Angeles. Starstruck, I mumbled something about being a fan and asked if I could take a photo of her. “Sure! Let’s take a selfie,” she said, leaning in close and beaming at my phone over my shoulder. In the photo, she is wearing a high-collared white blouse and a bowler hat.
She looked great, because she was great. La-di-da forever.
