Diane Keaton’s Looks Are Proof That Personal Style Never Goes Out of Fashion
A look back at Diane Keaton’s most iconic outfits and the signature elements that made her style timeless.
I’ve always admired Diane Keaton’s style, but since her passing I’ve been thinking about it in a deeper way. In a world obsessed with trends and reinvention, her wardrobe always feels refreshingly steadfast. She’s worn variations of the same silhouettes for decades, and instead of feeling repetitive, it feels powerful—like a reminder that knowing yourself is the ultimate fashion advantage.
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.
What makes her style so enduring isn’t just the clothes themselves, but the confidence behind them. She dresses for herself, unapologetically, and that’s exactly why her looks still resonate. Looking back at her outfits now feels less like a history lesson and more like a masterclass in personal style done right. Below, the 32 looks I beg you to remember when thinking of Diane Keaton.
Style Notes: Borrowing from menswear only works if you commit and Keaton always did—lean into sharp tailoring and keep everything slightly oversized.
Style Notes: The secret to effortless layering is sticking to a tight color palette (hers is a quite nostalgic moment).
Style Notes: The iconic look and celebrated quirky style of the character Annie Hall was all Diane Keaton.
Style Notes: Keaton won her Oscar for her performance in Annie Hall wearing a beige blazer, pleated skirt and knit scarf.
Style Notes: A relaxed suit always looks cooler slightly undone—think open collars, pushed-up sleeves, and a bit of nonchalance.
Style Notes: These leather trousers are doing all the work. Major!
Style Notes: Through the '80s, she began wearing oversized menswear-inspired pieces and outerwear, along with her signature big hat.
Style Notes: The '90s saw her wearing a lot of berets—from leather versions to this white one she chose on repeat.
Style Notes: When in doubt, anchor your entire look with one oversized accessory—it does all the talking for you.
Style Notes: Master of belts, she uses one outside of her leather jacket and silk scarf.
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.
Style Notes: This polka-dot jumpsuit look is a true winner, matching her shoes and her hat with Chanel-style strands of pearls.
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.
Style Notes: With her mother at the Golden Globes in 1994, Diane Keaton's OTT collar is almost eclipsed by her belt.
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.
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.
Style Notes: In her take on the white button-down–and–satin skirt combo.
Style Notes: Skip the expected evening dress—tailored suiting on the red carpet will always feel sharper and more memorable.
Style Notes: Out of the early noughties and Diane swaps into all-black leather in 2014.
Style Notes: In keeping with her love of houndstooth, her fitted jacket and white socks tone back her leather pencil skirt.
Style Notes: Always evolving her personal style, a new uniform is born consisting of a suit, large belt and even larger hat.
Style Notes: Here is a camel version of said uniform.
Style Notes: Maxing out in a checked coat and oversized bowler hat.
Style Notes: As casual goes, she still keeps the bar high with a chic leather jacket and roll-neck.
Style Notes: She sat front row with Tracee Ellis Ross at the latest Rodarte show.
Style Notes: Making monochrome exciting again, she pairs her houndstooth trousers with a longer jacket and fab white boots.
Style Notes: About a month ago, we were blessed with her #OOTDs like this one.
Style Notes: Perfection in her flame boots for her recent appearance on the Ellen show.
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.
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.
Style Notes: Sometimes all you really need is an all-black ensemble.
Pieces Diane Would Love:
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