Diane Keaton Style Secrets: From Annie Hall to Red Carpets – Menswear Inspired Fashion Icon (2025)

How Diane Keaton Invented Her Singular Style: Audacious, Gutsy and Independent

Diane Keaton, the ultimate cool girl of the 1970s, redefined menswear-inspired style and remained a fashion icon for nearly half a century. Her unique sense of style, both on-screen and off, was a blend of uncommon, fun, and age-appropriate elements that always felt true to her personality. Keaton's legacy is celebrated in the book 'Diane Keaton: Fashion First,' where she credits her mother as her style inspiration.

Keaton's breakthrough came with the 1977 film 'Annie Hall,' which won her an Oscar for Best Actress. The film's fashion, a mix of menswear-inspired pieces layered artfully, became a defining trend of the late 1970s and continues to be referenced in fashion today. This look was a collaboration between Keaton and costume designer Ruth Morley, who initially envisioned a less-defined character. Director Woody Allen intervened, allowing Keaton to control her on-screen style, resulting in a wardrobe that blended vintage finds, personal items, and pieces from Ralph Lauren.

The New York Times praised the trend, noting the 'Annie Hall look' was appearing on the streets with increasing frequency. Morley described the character as a girl who was 'little confused but not a hippy; she’s unusual, she’s trying to find herself.' This quote also reflects Keaton's own sense of self, as she consistently expressed her identity through her fashion choices.

Keaton's personal style was evident in her on-screen looks, from menswear-inspired tailored trousers and jackets to her love for accessories, especially hats. She played strong, confident women who found their inner strength throughout their stories, and her fashion choices inspired women of all ages.

On the red carpet, Keaton embraced her unique style, pairing jackets with statement skirts, statement shoes, and essential accessories like bowler hats and berets. Her favorite designers included Ralph Lauren and Giorgio Armani, who dressed her for the 1978 Academy Awards and the 2004 and 2014 Golden Globe Awards. Keaton's style evolved, incorporating pieces from Thom Browne, whose slim and forward-thinking menswear aesthetic aligned with her signature look.

Keaton's impact on fashion and her unique style will be remembered, as she consistently marched to the beat of her own drum, exuding authenticity and individuality throughout her career.

Diane Keaton Style Secrets: From Annie Hall to Red Carpets – Menswear Inspired Fashion Icon (2025)
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