The aesthetic legacy of Diane Keaton – the master of androgynous dressing
Diane Keaton, in her 2024 book Fashion First, reflects on the timeless allure of that totem of men’s style Cary Grant. “I wrote down two of his famous quotes. Number one: ‘Clothes make the man.’ And number two: ‘I pretended to be somebody I wanted to be, and I finally became that person.’ I had no doubt I could be the person I wanted to be if I applied Cary Grant’s concept.” That she did, in spades, until her death at the age of 79 last October.
The Oscar-winner’s style legacy lives on, however, thanks in part to the Bonhams auction of her estate which began on Monday, and is selling a range of fashion pieces – some of which have gone down in red carpet history – alongside memorabilia such as her script for Annie Hall, contemporary art and furniture from her Sullivan Canyon home.
I’m here, at the Bonhams HQ on a nondescript stretch of West Sunset Boulevard, the rolling Hollywood Hills in the distance, to see some of the pieces in person; a stovepipe hat, rustic throws and retro signs, as well as a container filled with very on-brand monochrome wrapping paper in a polka dot pattern. Keaton had her own aesthetic so absolutely that it even applied to her gift wrapping, it seems.
Other lots – including the checkered Ralph Lauren coat she wore to the 2020 Academy Awards, a Gucci sequinned suit in black, a rare moment of glitz for the normally androgynous dresser, and her bowler hat, symbolic of her Charlie Chaplin approach to dressing – are housed at Bonhams in New York.
Keaton styled a checkered Ralph Lauren coat with a bowler hat during New York Fashion Week in 2023 - Paul Morigi
It was a singular take on style that was entirely at odds with princess-y dressing and the siren gowns which were the received template in how Hollywood actresses presented themselves, bar rare exceptions like Marlene Deitrich or Katherine Hepburn. Keaton followed in their (brogue-shod) footsteps; tailoring formed the backbone of her wardrobe, a “borrowed from the boys” aesthetic that she made entirely natural and her own.
She cemented that approach in 1977’s Annie Hall, so much so that Woody Allen told the costume department to leave her to her own devices; Keaton created the character by melding the costumes with pieces from her own wardrobe.
With Woody Allen in the 1977 film Annie Hall - Bettmann
“I look back on Annie Hall and can’t talk about that movie without talking about the fashion. It was everything to me,” Keaton once said. “I loved being able to dress like myself. My muses were the women of New York City who were walking the streets of Soho in baggy trousers and a blazer.”
She evolved a signature style built on the tenets of men’s suiting, waistcoats, but nipped for her proportions, shirting, ties, syrupy, oversized trousers in pinstripes and checks, and of course those suits. “There are so many wonderful things to love about a suit,” she once wrote. “The pants don’t have to be too tight, neither does the jacket. I like my sleeves to go down long, to cover me up. Suits make me feel comfortable.”
Certain designers finessed suiting for women better than others, and soon the gravitational pull between Keaton’s defined sense of style and certain brands formed sartorial unions; Giorgio Armani, known for his fluid tailoring, dressed the actress for the red carpet after she found fame in Annie Hall, as did New York suiting wizard Thom Browne years later, in the Noughties, it was Ralph Lauren with whom she had the most enduring relationship; his all-American designs for women were in perfect step with her sense of dressing, a kind of Wall Street wallflower. Keaton learnt, over the years, certain tricks in how she adapted the tailoring to work for her boyish, elongated frame; belts, a vast collection of belts which she once broadcast on social media, to lend a waist on her lean physique, as well as the signature hats that topped off her look. Likewise polo shirts, which acted as an alternative to shirting.
Keaton evolved a signature style built on the tenets of men’s suiting, shirting and ties (photographed above in 1996) - Bob Grant/Fotos International/Getty Images
While Keaton wore floor-length skirts – particularly from the Noughties onwards – they were never too feminine ; rather they were sweeping affairs in heavyweight wools, a perfect balance to the nipped-in tailored jacket up top.
Oversized mannish coats were her equivalent of a red carpet dress, the silhouette and sense of formality were similar. While her clothing, like her home interior design, was mainly monochromatic, she relished detail of print and pattern; see the appreciation of houndstooth and pinstripes, of tartans and Prince of Wales check. The effect is very British countryside (which, as it happens, is textbook Ralph Lauren).
Other surprising elements from seeing the lots in person are the little details like how architectural some of the coats are, to lend sculptural shape to her slender frame. Likewise the shoes, which are either in chunky boot form or perilously high heels.
The pieces in the Bonhams auction are a reminder of just how distinctive Keaton was. As a sign that once decorated her home reads “Look, we don’t have that much time”, she made a lasting style impact and aesthetic legacy with hers.
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