Diane Keaton’s Quirky-Cool Fashions Never Cease To Inspire

The epitome of signature style.

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Diane Keaton Thom Browne Paris Fashion Week 2023

For some stars, it takes years to hone a signature sense of style — and it’s pretty standard to experience some missteps along the way. One celebrity who has seemingly never struggled with this? Diane Keaton, whose most iconic fashion moments are nearly too many to list.

Over her 50-year long career in show business, Keaton has established herself as one of the strongest presences in red carpet history — and that’s mostly due to the fact that she’s always danced to the beat of a different drum. Some of her go-to fashion staples, like bowler hats, long necklaces, gloves, and of course menswear never cease to stand out among the usual glamorous gowns. And after all these decades, she’s still sticking to exactly what she likes. Pretty iconic, actually.

The actor’s sense of style is so strong, she’s become synonymous with certain looks. And that’s exactly what makes her such a fashion muse. Over the years she’s built strong relationships with some of the most established designers in the business, like Ralph Lauren, Comme des Garçons, and Thom Browne, who know exactly how to highlight her quirky-cool sensibility.

Keaton’s penchant for timeless staples like well-tailored suits, crisp button-ups, turtlenecks, and leather trenches has also allowed her style to stay so consistent and so relevant over time. In fact, even her decades-old ensembles are still revered as the most memorable in fashion history. Want proof? Ahead, find 16 of the most iconic looks from this often imitated, never duplicated style star — beginning as early as 1976.

The Academy Awards, 1976

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In a sea of glittery gowns, the presenter’s white Richard Tyler suit with striped button-down and polka dotted tie was a major standout. To this day it’s considered to be one of the most iconic looks in Oscars history.

New York, 1988

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Keaton’s slouchy gingham jacket was the star of her out-and-about look in 1988. But underneath, her combination of ultra high-waisted pants, white blouse, and oversized flower accoutrement (perhaps an inspiration for Carrie Bradshaw’s signature accessory?) was just as chic.

Scleroderma Research Foundation Benefit, 1993

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The actor strayed from her usual black-and-white palette (and menswear staples) for a charitable event in 1993. In a green and white polka dot maxi dress, with white oxfords, a white beret, and long pearl necklaces, she still displayed her quirky-cool and out-of-the-box style.

I Am Sam Premiere, 2001

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Keaton also embraced a bold color while attending the I Am Sam premiere in 2001. She wore a red leather trench and matching beret with a black skirt and two more of her staples: a turtleneck and oversized belt.

The Golden Globes, 2004

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To accept her Best Actress award for Something’s Gotta Give in 2004, Keaton wore a form-fitted white Nehru jacket over a long tulle skirt. She completed the all-white ensemble with pointed booties, gloves, and her favorite jewelry style — navel-length pearls.

The Academy Awards, 2004

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The Oscar nominee turned up to the ceremony in her signature menswear style. Her Ralph Lauren ensemble featured her love for pattern mixing, with a striped vest and polka dotted tie and matching pocket square. She finished off the look with pointed wingtips, a bowler hat, and black leather gloves.

The Golden Globes, 2005

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For the 2005 awards show, the The Family Stone star was business on top, party down below in a tailored grey blazer and black tulle skirt.

The Hollywood Film Festival Awards, 2005

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The Hollywood Film Festival Award honoree donned a red plaid skirt with a black turtleneck for the ceremony. She also opted for a shorter length skirt, showcasing her black fishnets and pointed black pumps.

L’Oréal Legends Gala, 2006

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In a long black turtleneck dress and multi-strand black beaded necklace, Keaton went for a sleek, elegant look for the 2006 soirée.

The Tonight Show, 2013

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For her talk show appearance in 2013, Keaton wore a fitted black skirt suit accessorized with an oversized black belt, black ankle boots, and chain link necklace.

Hammer Museum Gala, 2015

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Keaton told the LA Times she wanted to “highlight her legs” with the ensemble she chose for the 2015 gala. Her shimmering Comme des Garçons sack dress showed a flash of skin and her and lace-up Chloe boots and black bowler hat completed the look.

Book Club Press, 2018

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While doing press for Book Club in 2018, the stylish septuagenarian selected a voluminous plaid skirt and long black jacket with a myriad of cross necklaces and black patent leather boots.

Poms Premiere, 2019

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Keaton showed her penchant for an exaggerated silhouette with her choice of ensemble at a press event for Poms in 2019. Fingerless black gloves, a wide black belt, and black boots finished off the look.

LACMA Art + Film Gala, 2021

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Gucci was an obvious choice for the 2021 art event, which was presented by the iconic fashion house. Keaton selected a sequin covered suit for a sparkling twist on her go-to menswear style.

New York Fashion Week, 2023

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Ralph Lauren is just one of the legendary designers with whom Keaton has built a long-lasting relationship over the years. Among her many looks she’s worn by the label is this belted plaid coat and striped grey pants, which nod to her appreciation for pattern mixing.

Paris Fashion Week, 2023

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Keaton was a standout front row guest at Thom Browne’s Paris Fashion Week show in 2023. The designer selected a seersucker suit and wicker Hector bag for a summery spin on her usual suiting.