I Tried Dressing Like Diane Keaton

The first time I watched Annie Hallmy boyfriend at the time fell asleep within ten minutes. I remember being initially annoyed but eventually grateful, because I must have paused the movie 100 times to take photos of Diane Keaton’s outfits. They’re so good that the plot feels inconsequential. To this day, whenever someone tells me my outfit reminds them of Diane Keaton, I blush, feel deeply fulfilled and cross everything off my to-do list. It’s happened like twice.

She makes me want to wear turtlenecks like undershirts, don suits and ties like they’re PJs, take my grandpa’s entire wardrobe to the tailor and never shop again. This infatuation doesn’t exactly make me special. Search “Diane Keaton style icon” in Google and you’ll get 613,000 hits. (Now 613,001.) So maybe it was a little selfish of me to claim her birthday as my own personal Halloween, but it’s one of the perks of the job.

Today she turns 71. She still kills it, always has. Look at her! The tinted glasses? The men’s trousers? The gullet accoutrement and little bowler hats? She must roll out of bed in all those layers. She’s so consistent. My favorite Keaton, though, is 1970s Keaton. In honor of her birthday (kind of) and my own interests (mostly), I decided to give three classic ’70s-era Keaton outfits a go.

Click through above to see the whole lewks!

The Full Suit

Here she is with an “unidentified man,” according to Google, looking 100x better than him and making me consider a nail-biting habit.

Rosie Assoulin jacket and pants, J.Crew shirt and tie

Here I am, looking slightly more Dad than Diane, but pleased with myself regardless because this suit is by Rosie Assoulin and made me feel like a million well-to-do bucks. I have no idea why I’ve never worn a tie.

The Annie Hall One


This is classic Annie Hall Diane Keaton, looking cuter than a billion buttons, wearing — as Amelia once put it — an outfit that, if not for her, might resemble the uniform of a T.G.I. Friday’s waitress.

Hm, let’s test this…


J.Crew shirt and tie, L.L.Bean pants, ASOS hat

Theory disproven. I actually look a hostess at an upscale Rainforest Cafe. I’m kind of into it, to be honest. My favorite part of this outfit is that the slacks are from L.L.Bean.

Sidebar: Why is it so hard to find a black waistcoat in this godforsaken city?!

The Six-Layer Moment

Here she is with another unidentified dude (ahem) looking like the cutest sentient onion on the planet (get it, layers). There really are six though: turtleneck, button-down, sweater, blazer, scarf, pants. Do pants count? I say yes. All tucked into cowboy boots.

J.Crew blazer and scarf, Madewell striped top over J.Crew turtleneck, Rachel Comey pants

Curiously, the one I nailed the closest piece-for-piece looked the most off. Whereas Keaton looks chic and comfortable, I appear to have just jumped off a very expensive horse. Clearly I’m not too mad, see: look-at-me hands. But I am sweaty.

Diane Keaton is the perfect example of the power of charisma where it intersects with a distinct sense of personal style. It supersedes a formula, is unexplainable. She wears a suit, looks casual. Wears pleated khakis, looks feminine. Wears cowboy boots, looks beachy. It’s impossible to imitate, which is probably why all of us want to so desperately.

Happy Birthday Diane Keaton! I really, really tried.

Photos by Krista Anna Lewis. Diane Keaton Photos via Getty Images.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

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