A woman in trousers is not often a mainstream celebrity style identity. From the time I decided in my early 20s that I would wear a lot of pants — for reasons ranging from rebellious (Western clothing!) to pragmatic (less waxing) — there have only been a small pool of heroes to choose from. Katharine Hepburn, Audrey Hepburn, and Diane Keaton became my holy trinity. While the Hepburns had their signature looks — Katharine championed wide-legged pants with button-down Oxford shirts and Audrey chose cigarette/capri pants with ballet flats — Diane Keaton wore her pants every which way. Cropped, wide-legged, boot cut, skinny, straight, and baggy.
I discovered Keaton the last, sometime in mid-2010s, when her Annie Hall (1977) look became the inspiration for a fashion season. While I only remember snippets from the film, her look — suit vests, men’s shoes, baggy pleated pants, knotted ties, and floppy hats — remains fresh. As has been endlessly chronicled since, it was a look that was very much Keaton’s own and it has been hailed as doing as much for pants in her time as Marlene Dietrich and Katharine Hepburn before her. This despite the fact that it had been around a decade since Yves Saint Laurent had introduced the tuxedo and pantsuit for women, and over half a century since Coco Chanel and Jean Patou had introduced pants for women to free them from restrictive clothing.
Diane Keaton and Woody Allen in the film ‘Annie Hall’ (1977). (Getty Images)
Diane Keaton at the 76th Annual Academy Awards in Los Angeles, the US. (Getty Images)
Women in tailored menswear have long been a socially and politically loaded image. Trousers symbolised male power and women who wore them were accused of being unfeminine. The aura of movie star glamour went some way in protecting them but even that didn’t fully shield Katharine Hepburn, Greta Garbo, and Marlene Dietrich from the labels. Trousers were also considered lesbian coded, while wearing full suits an assault on male identity and simultaneously a feminist issue of giving into male dominance. (This doesn’t apply to jeans or track pants, which are considered more unisex.) Damned if you do, damned if you don’t. The easiest option, and one that is still followed, was to only wear them some of the time, to let yourself be seen often enough in ‘feminine’ attire to offset the masculine.
But Keaton made her identity all about the menswear, right down to the shoes. She often took to the red carpet clad in tuxedos, three-piece suits, and spats. In the process, she created an alternative glamour, a version of modest fashion, and used every trope of what was unattractive in women and flipped it on its head. Besides her eclectically layered menswear, the oversized jackets, dangly neckties, layers of sweaters and vests, and cowboy boots, she also wore glasses and bowler hats.
Actor Katharine Hepburn. (Getty Images)
Actor Audrey Hepburn in 1953. (Getty Images)
The look she created was very much her own, one that could range from androgynous to asexualised to feminine. Of course, the fact that there was a history of skin cancer in her family makes her choices not only sartorial but also practical. She was herself diagnosed twice: with basal cell carcinoma at age 21 and squamous cell cancer decades later.
While Annie Hall’s androgynous style might have catapulted Keaton to fashion fame, it was not one that she stuck to all her life. You only need to look at her outfit to the Oscars of 1978, when she won Best Actress for Annie Hall, to see how soon she changed it up. She wore a swingy, voluminous mid-calf skirt over straight pants topped with a double breasted Armani blazer — a kind of layering that has never reached the mainstream and would leave current red-carpet watchers aghast.
Diane Keaton during 50th Annual Academy Awards in 1978 in Los Angeles, the US. (Getty Images)
In a video on her Instagram, she was seen talking about how very interested she was in fashion. What’s left unsaid was her willingness to take risks and try something new. Over the years, Keaton’s showed off her grey hair, eschewed cosmetic surgery, and never had a stylist. She played with volume often, especially when wearing skirts or dresses, and she did wear them, with as much pizzazz as she did trousers. She enjoyed a good anti-fit and often layered it with long coats. She mixed plaids and pearls, boots and blazers, cravats and big belts.
The introduction of pants was one way for Chanel to champion comfort and freedom; Katharine Hepburn famously skateboarded in hers, and Diane Keaton, perhaps, used that freedom to pursue anything that interested her. Besides being a Hollywood star, she wrote three memoirs, Then Again (2011), Let’s Just Say it Wasn’t Pretty (2014), and Brother & Sister: A Memoir (2020), and published numerous photography books, hers, others, and of found photographs. She pursued photography, shot a series of hotel interiors for Rolling Stone magazine, which then became the book Reservations, published by Knopf in 1980. The geometry of the black and white photographs inside finds an echo in her often monochrome clothing, checks and stripes.
Diane Keaton also did up houses, was responsible for preserving two Frank Lloyd Wright buildings, and published books about interiors, The House that Pinterest Built (2017) and California Romantica (2007). She adopted two children in her 50s, released a music single, and became an Instagram star.
Actor Diane Keaton in 1996. She wears a purple & black striped suit, bowler hat, and, around her neck, wears a large black crucifix. (Getty Images)
Over the years, I only saw Keaton on Pinterest and sometimes on red carpets, and was always struck by her genuine interest in fashion and putting clothes together. You can see when someone is having fun; not caring about always getting it right. That was Keaton’s biggest gift to me and her many fans, to enjoy the process of dressing up, to experiment, and not care if it always lands.
In her book, Fashion First (2024), she says, ‘I wanted my clothes to scream, Hey! Look! Look over here!’ but, perhaps, this was the only thing she was unsuccessful at — yes, people looked at her and admired her clothes and style, but only because they were part of her, not because they were clothes that screamed for attention. She wore them, they did not wear her.
The writer is a fashion commentator and author.
Published – October 18, 2025 07:18 pm IST
