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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. Related stories:   Here’s Looking at You, Kid: Iconic Movie Fashions Single and Successful: Ten Women Who Redefined Spinsterhood Life, Take Two: Five Remarkable Late Bloomers
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Early 1970s
1977
1977
1970s
1987
2006
2008
2009
2010
2011
2011

2009

Dusting off a few of the looks that made her famous, Keaton posed for More magazine in a tailored tuxedo and a revamped bowler’s hat thirty-two years after Annie Hall’s release.

1977

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.

1977

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

1970s

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.

1987

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.

2006

These days Keaton tends toward more tailored and figure-flattering silhouettes, but her styles are just as sharp as ever—if not more so. With her eye for color, proportion, and detail it’s no surprise that she landed the cover of Architectural Digest.

2008

Keaton’s love affair with polka dots continues at an event for the International Center of Photography in 2008.

2009

Dusting off a few of the looks that made her famous, Keaton posed for More magazine in a tailored tuxedo and a revamped bowler’s hat thirty-two years after Annie Hall’s release.

2010

Keaton pairs a sleek leather tunic with leggings, heels, black nail polish, and chunky frames for fresh, ultra-modern twist at the premiere of Morning Glory in 2010.

2011

Crisp white button-down shirt: check. Black trousers: check. Wide-brimmed felt hat: check. Polka dots: check. We can be pretty sure Keaton styled herself for this Vogue photo shoot with Annie Leibovitz last month, right down to the polka-dot finger nails!

2011

After a lifetime of looking fabulous on her own terms, it makes sense that Keaton landed a modeling contract. The only thing that doesn’t make sense is that it took this long. So far, just like the Vogue photo shoot earlier this year and Annie Hall before that, Chico’s seems to have taken cues from Keaton when it comes to styling the ad campaign. Now if you’ll excuse us, we need to go buy some leopard-print gloves and a new beret.

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