The intensity of the shock and dismay at the death of Diane Keaton, who was just 79, left one thing very clear: Her spirit and her style made a huge impact on generations of women. I say women, because (straight) men don’t seem to quite “get” her – unless they happen to be former paramours Woody Allen, Al Pacino or Warren Beatty – seeing only her quirky and whimsical side, and her great beauty. But women? We saw something else – the possibility that you could be happy on your own. She was famously single even through the aformentioned series of very high-profile romances, declaring she never wanted to be a wife. Most importantly, she proved you could be happy presenting your true, authentic self to the world, not some mask built to conform to it.

Keaton did not dress for the male gaze. She was a complete original, a trailblazer, for this simple fact. As Meryl Streep said in her tribute to Keaton at the American Film Institute: “She was possibly the most covered up woman” of all time. Starting with her Annie Hall character, Keaton borrowed from the boys and gave the elements – bowler hats, vests, ties, belt, clunky Oxfords – her own twist. Bette Midler said in a tribute this weekend that Keaton was “without guile,” which identifies why her fashion sense worked so well: Her kind of visual wit only works when done with complete authenticity.

She kept her colour palette simple: black and white with some tweed or checked pattern in those tones thrown in. The effect of a strict palette made her memorable, and allowed her personality to shine through more. She appropriated Marlene Dietrich’s tuxedos and Katharine Hepburn’s turtlenecks, tributes to the iconoclastic, boundary-pushing, strong female role models that came before.

Fashion was pure self-expression for Keaton, who incorporated vintage, embraced oversized jackets and belted them with giant cinching belts, and layered skirts over pants. Her skirts were always mid-calf long, sometimes multiple.

Keaton was a collaborator/muse to many directors, beginning with Woody Allen, who famously created Annie Hall for her and allowed her to infuse the character with her own fashion sense. Memorably, she showed up to the 1978 Oscars where she won the best actress statuette for that role in a double-breasted Armani suit jacket, two linen tiered skirts layered over trousers and scrunched socks. A pink flower boutonniere punctuated the look. 

Her years with Warren Beatty included a lush take on the Bolshevik Revolution in his 1981 epic Reds; she imbued her character, journalist/suffragette Louise Bryant, with her own brand of transformative modernism. The clothes she wore for the film’s circa 1917 setting still look modern. Then there was her work with Nancy Meyers, notably in the 2003 film Something’s Gotta Give. Two decades later, that wardrobe, heavy on white oversized cable-knits, inspired the “Coastal Grandmother” look for a new generation.

She didn’t care if the look was not traditionally sexy, or some people might think it weird or all together “too much.” Keaton applauded women who were too much, she encouraged and goaded all of us to stop trying to be perfectly in line with trends or falling victim to designer envy. She encouraged us to be ourselves, to trust our own instincts, to wear what made us happy and comfortable. Zoomerist is fixated on the fact that confidence is what creates great style, and Diane Keaton was the patron saint of confidence for women, at every age. She got more powerful, and more stylish, if possible, as she got older.

All her looks, on- and off-screen, remain timeless. Here are some by-the-item suggestions for how to dip into her closet, inhabit her vibe and pay tribute to her freedom of spirit. 

Bowler Hats

Keaton’s most signature style element, the bowler hats she wore in Annie Hall, were likely found second-hand. Today’s vintage stockpiles of old-school men’s hats are most likely depleted. Look, Amazon is chock full of knockoffs but low-quality felt feels like a sorry tribute to a fashion icon. Splurge instead on a real piece of head art. Toronto has David Dunkley Fine Millinery, a place to find everything handmade, including men’s classic shapes and custom.

For an online option, try old faithful (since 1932!) Montreal hatters Henri Henri.

Great Big Belts

The best way to wrangle oversized men’s jackets (and women’s styles have been trending oversized for several seasons now) is to cinch them with a great big belt. Keaton toyed with proportion by using belts to exaggerate her many layers of clothing. This bridle style by Canadian belt company Brave adds interest with a silver hooped buckle.

Vests

Of course, you can find many random men’s vests on the thrift market but spending a bit gives your look grown-up polish. The Canadian suiting masters, Smythe, have a terrific long black waistcoat in store right now. You can also cruise the racks at Zara for sleek, modern options.

Turtlenecks

Turtlenecks are an often forgotten basic wardrobe layering piece, perfect for Canadian winters. But since they can get worn out and baggy easily, it’s an item we need to restock. Hence, save your cash for great shirting, and grab an easy ribbed option, like these ones at Old Navy and Uniqlo.

Menswear-Style Shirts

The best borrowed-from-the-boys (but fit-for-a-woman’s-body) shirting will always be from Kim Newport Mimran’s Pink Tartan. These are solid, eternal basics to invest in. Here is a fun option from this season in honour of Keaton, with adorable retro ric-rac black trim on classic white.

Loads of Pearls, Piles of Crosses

Now here is where the flea market finds really come into play. Yes, you could get a great basic (and surprisingly affordable)  Tiffany trio of long necklaces as the base for the neckfull of pearls that was Keaton’s signature embellishment. But the right move would be to mix in found costume strands to bulk it up. There are loads of fun options on Etsy, too. As to silver crosses (again, Keaton wore multiples on long chains), these look best when they are a real mix of styles, some found, some new. 

Reflecting on the impact of Diane Keaton on our attitude and style, we have a lot of gratitude for the paths she opened up for self-exploration and self-expression. Adopting a few of her favourite things and incorporating them into our wardrobe rotation seems like a fitting way to keep her fierce independent spirit alive.