A fashion icon for the ages, the late Oscar winner was unapologetically herself, with a penchant for menswear staples, belted waists, brimmed hats, turtlenecks, chunky ankle boots and a strict black-and-white color palette.
Meryl Streep honored Keaton at the 2017 American Film Institute Lifetime Achievement Awards, describing her friend as “arguably the most covered-up person in the history of clothes” yet “transparent” when it comes to her personality and performances.
Keaton never employed a stylist, instead approaching everything — from a dog walk around Brentwood, Calif., to an awards show red carpet — with the same sartorial point of view.
As the titular character in “Annie Hall,” Keaton showed off her timeless personal style. Alamy Stock Photo
The actress was one of the few whose personal style managed to inform her onscreen personas. And considering Woody Allen famously asked her to dress herself for “Annie Hall,” that comes as no surprise.
From Hall’s borrowed-from-the-boys styling to Erica Barry’s turtlenecks in “Something’s Gotta Give” to Sybil Stone’s full, belted skirts in “The Family Stone,” the closets of Keaton and her characters morphed into one.
Though impossible to encapsulate the legend’s iconic style in a single slideshow, scroll through some of Diane Keaton’s most beloved looks below.
1970: Long before the film called “Annie Hall,” there was the original Annie Hall. Seen here with then-boyfriend Woody Allen, Keaton wears a button-up shirt, jeans and dark jacket just like her character’s. Ron Galella Collection via Getty Images
1974: As Kay Adams in “The Godfather: Part II,” Keaton kick-started her longtime love affair with turtlenecks. Corbis via Getty Images
1974: Another style similarity between Adams and Keaton? A fondness for hats — wide-brimmed and bowler, raffia and wool. Alamy Stock Photo
1976: Keaton attended the Academy Awards wearing a white suit Annie Hall would cherish, styled with a striped button-up and polka-dot tie. Getty Images
1977: Allen famously asked the actress to style herself for “Annie Hall,” resulting in a character that feels quintessentially Keaton. Bettmann Archive
1978: Keaton won an Oscar for her role in “Annie Hall,” wearing a midi skirt, button-up shirt and blazer — a look that we would see regularly on the star for a lifetime to come. Disney General Entertainment Content via Getty Images
1985: While Keaton loved to layer turtlenecks with sweaters and blazers, she also relished a necklace moment, as seen here with multiple strands of pearls in various sizes. Ron Galella Collection via Getty Images
1997: Keaton nodded to her final “First Wives Club” look at the Academy Awards the following year, choosing a double-breasted white pantsuit with matching boots and gloves. Getty Images
2000: In a look that’d soon become her signature, Keaton wore a black-and-white gingham full skirt, white button-up shirt and a wide black belt on “The Tonight Show with Jay Leno,” adding her signature gloves, boots and even tinted glasses. NBCU Photo Bank/NBCUniversal via Getty Images
2014: On “The Tonight Show Starring Jimmy Fallon,” Keaton married some of her favorite accessories with a classic tux, plaid tie, wide belt and bowler hat. Theo Wargo/NBC
2017: The American Film Institute honored Keaton with a Lifetime Achievement Award and, feted among friends, she chose a black turtleneck and full black skirt topped with a contrasting white coat and one of her favorite wide waist belts. She wore a black hat and chunky heeled booties for a little added flair. Getty Images
2018: Keaton’s children, daughter Dexter and son Duke, followed her fashion lead at the premiere of her movie “Book Club,” wearing black and white to match their mom’s plaid skirt, black turtleneck, white jacket and combat boots. FilmMagic
2019: Opting for a plaid pantsuit, Keaton slipped into her signature black turtleneck and piled on countless silver cross pendants. FilmMagic
2019: Keaton spent the better part of the year (and then some) chronicling her daily outfits; here, she’s seen in head-to-toe white by Ralph Lauren. diane_keaton/Instagram
2019: Keaton used her captions, always in all caps, to reflect on her wardrobe choices and offer a look inside that super-quick brain of hers. Of this ensemble, she wrote, “THIS LOOKS LIKE I’M WEARING A TENT. OR IS IT A CONE? IT’S THE SHOES THAT STAND OUT, THEY’RE SPECIAL.” diane_keaton/Instagram
2019: Pared down, but still very much her signature style. Here, Keaton wears wide-leg jeans and her go-to black turtleneck, along with a grommeted belt, sunglasses and a bowler hat. Of the jeans, she wrote, “I’VE NEVER RECEIVED MORE COMPLIMENTS ON ANYTHING I’VE EVER WORN IN MY ENTIRE LIFE.” diane_keaton/Instagram
2020: Ringing in the New Year in style, the actress kept her face covered with one of her many hats. In a polka-dot skirt, black turtleneck and chunky boots, the look is everything Keaton loved. diane_keaton/Instagram
2022: A longtime Ralph Lauren fan, Keaton attended the brand’s spring 2023 show wearing high-waisted pants, a high-necked shirt and long coat to match. Getty Images
2022: In all black, Keaton beamed in her full skirt and turtleneck, nipped in at the waist with a belt and finished off with a hat. Getty Images
2023: In attendance at the Ralph Lauren spring 2024 show in New York, Keaton chose a plaid coat atop her turtleneck, letting her gray pinstriped pants peek out from below. GC Images
2024: In one of the last photos taken of the star, Keaton smiles at the paparazzi in Brentwood, dressed in an all-black menswear look that embodied her inimitable personal style. GC Images
