Diane Keaton Was a Fashion Icon: See 18 of the Late Star’s Delightfully Quirky Looks

The 'Annie Hall' star, who just died at 79, once said she had 'endless fashion mistakes,' but we beg to disagree

By Abbey Bender October 13, 2025

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Keaton remained remarkably consistent in her dedication to hats, ties, belts, blazers, turtlenecks and trousers, and her ragtag take on preppy style inspired multiple generations of women. In today’s age of designer outfits dictated by celebrity stylists and brand deals, Keaton’s dedication to rocking her own distinctive look on every red carpet feels more vital than ever.

Diane Keaton will be deeply missed, so we’re honoring her memory with a look back at some of her greatest outfits.

1. All tied up

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Keaton wore ties even before she made them a trend in Annie Hall, as evidenced by this photo of her at the 1976 Academy Awards. Her penchant for menswear was often compared to classic Hollywood actresses like Katharine Hepburn and Marlene Dietrich, and she cited Cary Grant as one of her biggest inspirations, writing, “I had no doubt I could be the person I wanted to be if I applied Cary Grant’s concept that ‘clothes make the man. Or, in my case, ‘clothes make the woman.’”
2. And the Oscar goes to . . .

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In 1978, Keaton won a well-deserved Best Actress Oscar for her performance in Annie Hall, and she showed up to receive her award in a distinctive outfit that featured not one but two skirts layered over pants and a pair of scrunch socks. The actress drew from her real-life style to create her signature character’s look, and she recalled that director (and her former boyfriend and frequent artistic collaborator) Woody Allen told her to “wear what you want to wear,” saying, “So I did what Woody said: I wore what I wanted to wear, or, rather, I stole what I wanted to wear from the cool-looking women on the streets of New York.”
3. Athleisure vibes

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Long before athleisure was a thing, the Godfather actress looked charming in a tracksuit in 1975.
4. Stripes on stripes

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A vertically striped coat paired with horizontally striped pants and checkered shoes might sound like a fashion faux pas, but in the ’80s Keaton made mixed-up patterns look effortlessly cool.
5. A pop of color

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Keaton often wore clothing in neutral tones but when she added color, she made it count, as seen here, when she intriguingly tucked a bright green silk scarf under the belt of her leather jacket in 1991.
6. Fashionably oversized

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Keaton loved an oversized blazer, as seen here in 1992. The First Wives Club star once quipped, “You could call a good two-thirds of my wardrobe an impenetrable fortress.”
7. Camel chic

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A camel coat is a fashion staple, but it's the baggy silhouette and big belt that make this 1993 look classically Keaton.
8. Pretty in polka dots

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On the occasions when the Father of the Bride star wore a dress, she favored vintage-inspired frocks rather than the sexy gowns of her peers. And of course, no dress was complete with some accessories, as in this 1993 look topped off with a beret, sunglasses and a pile of pearls.
9. Goth girl

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Keaton’s Annie Hall fashion was known for its spin on the preppy look, but she later welcomed more alternative style into her closet. When wearing an all-black ensemble topped with crucifix during a 1993 Tonight Show appearance, the Family Stone star served a witchy goth look.
10. Luxurious leather

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In 2000, Keaton stepped out in an artsy double-breasted leather coat paired with one of her signature belts. The Book Club actress once said “Belts are our saviors,” and shared that she liked wearing them because they helped shape her waist and made her stick-straight figure more defined.
11. Red-carpet tartan

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The Looking for Mr. Goodbar star paired a tartan skirt with a black turtleneck (one of her most-worn items), fishnet stockings and opera gloves in 2005, making for a surprisingly seductive outfit.
12. Puttin’ on the Ritz

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Keaton loved oversized clothes, but she also appreciated Old Hollywood-style tailoring, as you can see from this sharp ivory tuxedo she wore at the premiere of her movie Mad Money in 2008.
13. A classic button-down

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There’s nothing more classic than a simple white button-down, and Keaton looked understatedly chic when she paired one with a long black skirt (and a belt, natch) in 2007. The actress told Vogue that she loved a black-and-white look because “you can add anything to it.”
14. Menswear to the max

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In a 2014 Tonight Show appearance, Keaton looked as Annie Hall-like as ever. Reflecting on the film, she once said, “I look back on Annie Hall and can’t talk about that movie without talking about the fashion. It was everything to me. I loved being able to dress like myself.”
15. Blue mood

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When Keaton chose something colorful, like this bright blue leather jacket she wore to the premiere of her 2015 film 5 Flights Up, it made a splash on the red carpet.
16. Numerous necklaces

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In a hilarious video shared on Instagram in 2023, Keaton called this 2019 look one of her “endless fashion mistakes” but the contrast of the many necklaces and chunky shoes with the plaid suit works better than she gave it credit for.
17. A trusty hat

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Keaton paired a voluminous black-white-striped dress with a bowler hat and belt at the premiere of her 2023 film Book Club: The Next Chapter. Hats were staple pieces for her, and she told Vogue that she had 40 of them in her collection and her black Baron bowler hat was her favorite.
18. An unexpected accessory

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Keaton was an expert in incorporating sly humor into her style, and in 2023, she did just that when she wore a seersucker suit, straw hat and platform oxfords, and finished the look with an adorable dog-shaped wicker bag. When Vogue called Keaton a style icon, she was characteristically humble, saying, “It’s an honor! Why me? I’ve been so fortunate and lucky,” and she’ll forever be on our fashion mood board.

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