I Wish I Dressed as Cool as This 73-Year-Old Hollywood Megastar

Last week, Diane Keaton disclosed—IN ALL CAPS—on Instagram that she has not worn colour in over four years. The confession came paired with a picture of her in a voluminous hazmat-orange dress while covering her face (#relatable). We've recently charted her new OOTD-style posts, thanking the style deities for such exclusive and completely authentic fashion advice from an actual style icon. Since posting her outfits more frequently, 73-year-old actress has become the ultimate influencer, simply because she already was one long before Instagram existed.

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Since her breakout role playing a version of herself in Annie Hall, Keaton's become the most highly referenced master of menswear for women. That iconic look—the relaxed khaki slacks, waistcoat, white shirt and tie—has never been beaten. Since then, she's evolved her look over and over while sticking to her very own slightly off-beat sense of style.

Through the '70s, she wore neutral layers of beige. In the '80s, she paired leathers together the way Canadians do denim and favoured massive overcoats and floppy hats. The '90s saw her many all-white ensembles, perhaps even inspiring the iconic dance scene in The First Wives Club.

Since then, we've seen her wearing berets, quirky frames, OTT belts and so much more. Over the years, Diane Keaton has proven how to make monochrome exciting while evolving her personal style by incorporating trends and new shapes into her look. Plus, she's unafraid to challenge celebrity fashion expectations.

Keep scrolling to trace the legendary woman of style that is Diane Keaton through her outfits starting from the 1970s up until this week.


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Style Notes: The iconic look and celebrated quirky style of the character Annie Hall was all Diane Keaton. 


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Style Notes: Keaton won her Oscar for her performance in Annie Hall wearing a beige blazer, pleated skirt and knit scarf. 


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Style Notes: With then-boyfriend Warren Beatty in a cord suit and matching tan belts. 


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Style Notes: These leather trousers are doing all the work. Major!


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Style Notes: Through the '80s, she began wearing oversized menswear-inspired pieces and outerwear, along with her signature big hat. 


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Style Notes: The '90s saw her wearing a lot of berets—from leather versions to this white one she chose on repeat. 


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Style Notes: Master of belts, she uses one outside of her leather jacket and silk scarf. 


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Style Notes: With her favourite accessory (her diary) in hand, this early '90s look is Diane's peak suiting outfit, complete with a polka-dot pocket square. 


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Style Notes: This polka-dot jumpsuit look is a true winner, matching her shoes and her hat with Chanel-style strands of pearls.


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Style Notes: 1994 pre-dated the iconic all-white outfits in The First Wives Club but was only the beginning of many more to come in Diane's real-life wardrobe. 


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Style Notes: With her mother at the Golden Globes in 1994, Diane Keaton's OTT collar is almost eclipsed by her belt. 


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Style Notes: 1997 was the year when she arrived at the Academy Awards with Steve Martin and a pair of white platform boots. 


Style Notes: But it was her suit and bowler hat in 2004 that made headlines and is still referenced as one of the most iconic Oscar looks of all time. 

Related: Diana Ross Circa 1970 Is Very on Trend for Right Now


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Style Notes: In 2004, she accepted a Golden Globes award for her performance in Something's Gotta Give—a film that gave us many things, but notably the most relatable crying scene ever.


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Style Notes: In her take on the white button-down–and–satin skirt combo. 


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Style Notes: In 2008, she gave us the shiniest version of her signature all-white look.


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Style Notes: Out of the early noughties and Diane swaps into all-black leather in 2014.


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Style Notes: In keeping with her love of houndstooth, her fitted jacket and white socks tone back her leather pencil skirt.


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Style Notes: Always evolving her personal style, a new uniform is born consisting of a suit, large belt and even larger hat. 


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Style Notes: Here is a camel version of said uniform. 


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Style Notes: Maxing out in a checked coat and oversized bowler hat. 


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Style Notes: As casual goes, she still keeps the bar high with a chic leather jacket and roll-neck.


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Style Notes: She sat front row with Tracee Ellis Ross at the latest Rodarte show. 


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Style Notes: Making monochrome exciting again, she pairs her houndstooth trousers with a longer jacket and fab white boots. 


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Style Notes: About a month ago, we were blessed with her #OOTDs like this one. 


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Style Notes: Perfection in her flame boots for her recent appearance on the Ellen show.


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Style Notes: Gwyneth Paltrow commented on this post, "I FEEL THAT I NEED TO BE IN THAT CLOSET WITH YOU," and we couldn't agree more. 


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Style Notes: She continues to promise us that not wearing colour can be exciting and she's right. Note the matching scarf at fab lace-up boots. 

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