Diane Keaton: Evolution of a Style Icon

In the era of celebrity stylists and glam squads galore, it's hard to tell which stars actually have a sense of style and which ones simply have enough money to look like it. Not so with Diane Keaton; the beloved actress, who revolutionized the way women dress with a men's tie and a baggy pair of chinos in Annie Hall, always shows up looking fabulous and quintessentially Keaton. Now, with a new book flying off the shelves and her first modeling contract at the age of sixty-five, Keaton's star is shining brighter than ever; or maybe we're just finally catching up to a woman who was always leaps and bounds ahead of her time. Take a look at some of our favorite fashion moments from the style icon over the last forty years.

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If there's one thing Keaton has mastered (besides acting, of course), it's the art of accessorizing. She rarely steps out without a well-chosen accent-a fun scarf, a statement belt, a pair of thick-frame glasses, or her signature bowler's hat-to elevate her look from ordinary to extraordinary.

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Unlike actors nowadays, who are styled, primped, and preened by a swarm of costume designers on set, Keaton styled herself and pulled from her own closet for her eponymous role in Annie Hall. The result was fashion history.

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Keaton eschewed menswear for a more bohemian, feminine look on the cover of Rolling Stone the same year Annie Hall was released.


Fashion rules are made to be broken, and nothing does that quite like an oversized white suit paired with a striped shirt and polka-dot tie. What's more, we're pretty sure a version of this 1970s-era suit walked the runway at fashion week this year.

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The jutting shoulder pads, the cinched waist, the power brief case: welcome to the 1980s, folks. This iconic look from Baby Boom was not quite as whimsical as the bohemian menswear-inspired ensembles of years prior, but definitely at the forefront of what was hot. And, look, she even worked in some polka dots because she's Diane Keaton.

See More of Diane's Looks Throughout the Years!

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