Diane Keaton’s Iconic Fashion: From ‘Annie Hall’ Menswear to ‘Coastal Grandmother’ Chic

On October 11, at the age of 79, the world said goodbye to Diane Keaton—a true legend known for her contributions to film, theater, and fashion.

Keaton, an eternal style icon and Oscar-winning actress, embraced her unique fashion sense with confidence. Her signature look included menswear-inspired pieces, cinched waists, wide-brimmed hats, turtlenecks, substantial ankle boots, and a classic black-and-white color scheme.

In 2017, during the American Film Institute Lifetime Achievement Awards, Meryl Streep paid tribute to Keaton, calling her “arguably the most covered-up person in the history of clothing” while also being “transparent” in her personality and acting.

Keaton took a personal approach to her style, choosing her outfits herself for every occasion—from casual strolls around Brentwood, California, to glamorous red carpet events. This consistent style philosophy made her stand out.

Her personal fashion choices were so influential they often shaped the characters she portrayed on screen. Notably, Woody Allen had Keaton dress in her own wardrobe for her role in “Annie Hall.”

Whether it was the menswear-inspired looks of Annie Hall, Erica Barry’s turtlenecks in “Something’s Gotta Give,” or Sybil Stone’s flowing, belted skirts in “The Family Stone,” Keaton’s wardrobe was a seamless extension of her characters’ closets.

While it’s challenging to capture the full essence of Keaton’s iconic style in just a few images, you can explore some of her most memorable outfits below.