Diane Keaton: Evolution of a Style Icon

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.

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.

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.

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.

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.

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

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.

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.

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!

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.