By Kasey Dugan

Dedicated to my stylish grandmother, Lucille.

Earlier this month, Hollywood legend Diane Keaton passed away from pneumonia. Lately it seems like we’re losing all the good ones, doesn’t it? Diane Keaton was one of the good ones. It’s not like I personally knew her beyond the screens she occupied in my home, although she seemed to have that effect on people. Her warm demeanor oozed through the screen and into our hearts, which is why her passing has been so troubling for longtime fans. 

From Annie Hall to First Wives Club to Something’s Gotta Give, Keaton has always delivered a leading woman with charisma and wit. And while I could go on and on about her list of star-qualities, both on-screen and in-real life, it’s Keaton’s style that I want to focus on today.

This highly curated collection of looks is yours for the taking. I hope it can teach you something about your own style, even if that means simply learning how to maximize your Keaton potential. Or if nothing else, let this list rekindle your love for constructing fall outfits. I know we’re tired of being marketed the same Zara sweaters in every TikTok video and Instagram reel. So instead, what if we tapped into our authenticity? What if we tried to tell people a story with our clothes?

That’s what I hope comes across for you in this list, dear reader: the courage to be yourself, no matter what’s trending or what other people like. I believe Keaton on-screen and off-screen embodies this better than anyone — so let’s dive in!

1) The Monochrome

I had to start off with my personal favorite: Keaton’s all white outfits in Something’s Gotta Give. In this star-stacked film, Keaton plays fictional playwright Erica Barry who finds herself in the middle of an eclectic love triangle. Okay, the plot is way more complicated than that — but we’re here for outfits! Keaton’s polished turtlenecks may be off-putting to aging womanizer Harry Sanborn, but they’re absolutely scrumptious to me. I love that she sticks to long sleeves and slacks - and she isn’t afraid to pair together warm-toned whites with cool-toned whites. She plays with textures and silhouettes without ever straying from her sleek blowout. Erica’s wardrobe tells a story of refined elegance and success — even if she is a little cautious with her heart.

I know this movie technically takes place during a Hamptons summer, but these outfits are absolutely autumn-appropriate. In fact, I’d say there’s nothing more chic than an all-white outfit in autumn. Who wants to follow that stuffy no-white-after-Labor-Day rule, anyway? 

If an all-white look isn’t your thing, try pulling off an all monochrome look in your preferred favorite color. As a pro-tip, I want to suggest wearing an all-monochrome outfit in your signature color. (And if you don’t have one, you should figure it out!) There’s nothing more chic than being recognized in your signature color.

2) The Print

These stills come from The Family Stone, a film that might be whackier than the book it’s based on. Nonetheless, Diane Keaton stars as polarizing matriarch Sybil Stone. I’m never sure how I feel about this messy plot, let alone the fact it is technically a Christmas film — but Keaton’s cozy, nostalgic outfits left a positive impression on me. The Stone house feels lived in; from half-drank cups of tea to half-read piles of books, Keaton emerges as a believable mother of four. I love that the costume team really explored prints in these looks. Her outfits may go unnoticed on screen thanks to the absolutely-bonkers script, but maybe we can finally recognize them here. 

In her first look, Keaton dons a huge skirt with polka-dot and abstract-flower embellishments. In her second, she layers a pinstripe-collared blouse over a white turtleneck — which really allows the stripes to pop. I adore that her bracelets are layered over the cuffs so we can appreciate their beauty. In her third look, Keaton keeps it casual in a camel-colored bathrobe on Christmas morning … but the striped scarf peeking out from beneath the collar is eye-catching. (I love the detail that she’s wearing a scarf and a bathrobe indoors — it must be a frigid morning in the Stone house!) Lastly, Keaton pairs an argyle cardigan over two more layers of knitwear. Her color palette, much like her home, is warm and nostalgic.

If you steal anything from this movie, let it be the looks and not the morals. Try adding an unexpected print into an otherwise one-dimensional outfit. It might make all the difference!

3) The Bold Accessory

According to Screenrant, Because I Said So surged on streaming apps after Keaton’s death was announced. Being transparent, I have not seen this one …  although based on the hot-and-cold reviews, maybe I should get around to it. Keaton stars as the meddlesome mother Daphne Wilder who is hellbent on setting up her daughter with Mr. Right. 

Daphne may or may not be an unlikable, control-freak mother —  but her outfits are undeniably chic. I famously love a neck-tie scarf, so this first look is doing a lot for me. The polka dot blouse adds a hint of whimsy as well. 

In her second look, Keaton wears a classic black-top and white-bottom … but that red flower is something else! I don’t have the context for this scene, but I hope she simply stuffed a flower into the hole of her waistbelt for no reason other than she can. That would be the ultimate testimony of mixing business with pleasure. 

In her third look, Keaton wears a black-blazer over an A-line skirt (or perhaps it’s a blazer-dress.) This one is more on-brand for Keaton’s real-life style (which we will get to in a moment), but I want to draw attention to the excessive layering of pearl necklaces. I have no clue if these pearls are real or fake, but this is a great reminder to bring back costume jewelry. It’s pure fun! That small touch truly livened up her dark silhouette.

Lastly, Keaton dons an extra-wide belt. If you’re able to pull off a large belt, do so fiercely and don’t look back. I love how it takes up a significant portion of the lower screen … you truly can’t ignore it.

My advice: rummage through your wardrobe and your trinkets. Break out the hats, the flowers, the belts, the scarves, the pocketwatches, the mismatched gloves. Dare to be different … that’s how true style is born.

4) Businesswear and 70s Flair

Obviously, it’s not a Diane Keaton lookbook if we don’t talk about Annie Hall. Most of today’s discussion on Annie Hall is centered on Keaton’s controversial friendship with longtime friend and co-star, Woody Allen. If you’ve gotten around to watching this 1970s romantic-comedy, you know it’s a bit of a surreal journey through time, musings, and relationships. 

Diane Keaton stars as the titular character, Annie Hall, a struggling nightclub singer who is the yin to comedian Alvy Singer’s yang. Annie Hall explores how love is absurd but real — irrational, yet necessary. 

Also irrational, yet necessary, are these outfits. Keaton stuns in menswear in nearly every scene. She struts through the streets of a too-cool New York with wide trousers, brimmed hats, and my personal favorite — a tie. She’s calm, and collected in her high-rise slacks and collared shirts. I adore small details such as her wool socks peeking through her strappy loafers. Also, her round-framed glasses are cute!

I know we’re all about the office siren these days, but maybe we ought to direct our attention to thrifting vintage menswear. These oversized, textured silhouettes carry swagger and sophistication that 90s businesswear attempted to emulate (a la 90s-does-70s). So why not go for the original 70s cut?

What I want you to take away from Annie Hall is relaxed silhouettes and earthy details. What’s great about these outfits is their flexibility. You don’t have to commit to a full suit — try incorporating a tie, for example, into your next unsuspecting look. I guarantee it will turn heads.

5) Layers and Whimsy

Last, but certainly not least, is Diane Keaton starring as herself. I want to point out that these images were pulled from paparazzi sightings and red-carpets, which may give us a glimpse of Keaton’s style, but not the full picture. We don’t know what Keaton looked like drinking her morning cup of coffee or harvesting rutabaga from her garden. Hell, I don’t even know if she had a garden. But I’d like to think she had a knack for clothes whether she was on the red-carpet or not.

Now that we got that out of the way — I truly encourage you to do a deep dive on Diane Keaton’s photographed “true style” because it is a gold mine. After analyzing dozens of images, I’ve chosen these four to demonstrate a consistent theme I noticed in her outfits: layers and whimsy. 

In her first look, Keaton matches a white beret to her white scarf and undershirt. As a fellow beret-owner, I feel vindicated seeing Keaton own one, too. Multiple, actually — skipping ahead to last look here, she pairs a black beret with a mesmerizing all-sequin suit. It’s such an odd pairing, but it works by adding a hint of bohemianism to a glamorous suit. 

In Keaton’s second look, she wears an A-line skirt (or possibly a dress) with a yellow-gingham pattern reminiscent of Cher Horowitz two-piece suit in Clueless. She pairs it with a dark leather jacket, but that’s not all — she pulled out the oversized lapels of her collar shirt to sit atop the jacket. This look is funky, fresh, and a little bit Vivienne Westwood. She just radiates coolness.

In her third look, Keaton’s baggy jeans are an honorable mention. But her checkered blazer and bowler hat are the true stars of the show. Did I mention I love her love of hats? This is such a great way to dress-up an otherwise so-so outfit. Everyone who is anyone wears a coat with jeans. But the bowler hat is that unexpected touch that gives Keaton edge.

I hope looking at Keaton's “true” style gives you the courage to be authentically yourself -- no matter which aesthetic, silhouette, or accessory catches your eye.