History of Diane Keaton's nonconformist style

On September 3rd, Diane Keaton: Fashion First (Rizzoli) landed on bookstore shelves, a book in which the actress explores her own style by retracing its aesthetic evolution from the set to real life. Some may remember Keaton for her role as Al Pacino's intelligent and loyal companion in the trilogy of The Godfather, where she played Kay Adams, while others identify her as a cinematic icon of female independence thanks to films like the comedy The First Wives Club. However, everyone, when they hear the name Diane Keaton, thinks of the star's unmistakable androgynous look as Annie Hall—a role that earned her an Oscar. It was 1977 when Keaton entered the collective imagination with the romantic comedy Annie Hall by Woody Allen, in which she played Alvy Singer's ex-girlfriend. Her on-set style, characterized by oversized blazers, vests, wide pants, and a tie, was a real revolution for the female wardrobe: in the preface to Diane Keaton: Fashion First, Ralph Lauren writes, «I’m often credited with dressing Diane in her Oscar-winning role in Annie Hall. That’s not true. Annie’s style was Diane’s style.» The designer’s observation was also reiterated several times by the film’s director, Woody Allen, who responded to the costume designer Ruth Morley's doubts: «She’s a genius. Let her do what she wants, let her wear whatever she likes.»

After the release of Annie Hall (1977), the looks Diane Keaton showcased in the film became a phenomenon in 70s women’s fashion, influencing generations of women to question gender stereotypes. The star's inspiration seems to stem from her genuine admiration for actor Cary Grant. “He was my idol, and I admired him immensely watching him in films; I wanted to imitate him. I love thick, structured suits. I think masculine is feminine,” the actress says. To design Annie, Keaton relies on layered looks enriched by accessories that highlight her individuality, such as glasses, gloves, and a vibrant bowler hat. The actress incorporates several layers of fabric as if each were an expression of a part of herself: the secret lies in adding, rather than removing. «If I had to describe my so-called 'street style,' I’d say: REMOVE MY ENTIRE BODY... Unfortunately, I need a nose and a mouth to live and breathe, but that doesn’t mean I have to show them,» she explains in Fashion First. It’s no surprise then that when asked which celebrity she admires for their style and aesthetic, Keaton answers Karl Lagerfeld. «Because he wasn’t afraid to cover up and neither am I,» she explains.

In the book, the actress also talks about her passion for flea markets and second-hand clothing shops, an interest inherited from her mother. Among the memories mentioned, Keaton also writes about not being allowed to wear the bowler hat to prom because her mother forbade it: years later, that same accessory would become a symbol of her nonconformist style. Unforgettable was 2004, when she sported it at the Oscars ceremony paired with a Ralph Lauren tuxedo, a polka dot tie, and heels. That same year, the actress appeared at the Golden Globes in an all-white look, composed of embroidered shoes, gloves, and a long pearl necklace. She also wore a wide tulle skirt, another staple in Keaton’s wardrobe. Often paired with wide belts at the waist, long skirts allow her to play with volumes and geometries. Memorable, for example, was the mermaid skirt worn in 2007 at the Lincoln Center in New York, or the one she showed off at the David Donatello Awards in 2018, not to mention the checkered skirt from the Golden Globes in 1994.

The harmony with Ralph Lauren's aesthetic has remained evident even in recent years, reaching a new peak at the 2020 Oscars when the actress wore a wool and cashmere coat with a plaid pattern, a belt at the waist, and a bowler hat—a nostalgic throwback to the golden years. Over time, Keaton has introduced bolder, almost edgy elements that might seem to differ from Lauren’s aesthetic but actually highlight the actress's unique personality. Examples include combat boots or the cross necklaces she wore at the premiere of Green Eggs and Ham in 2019, as well as at the premiere of Crimes of the Heart in 1989, or the leather inserts, from simple gloves to the total leather look worn at the premiere of What Women Want in 2000. Surely, Keaton’s style choices have always conveyed strong messages of courage and independence, some more explicit than others. One example? The hat with the words “Vote bitches” worn on the street in 2020. An accessory that, even today, could still come in handy.