I Tried Dressing Like Diane Keaton

I know it’s her birthday but it kind of feels like mine.


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.

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  • Eva Skewes

    Haley, if you ever find a reasonably priced women’s waistcoat, please let me know. I’ve wanted one for aaaaages. Sadly, whenever I see one it’s too slim at the top, like it’s a boob shelf.

    • Andrea Raymer

      I just buy mens clothes. All of my blazers are for the mens section!

    • Haley Nahman

      Was at 10 Ft Single the other day (thrift store in williamsburg) and there were a tonnnnnnnn

  • Quinn Halman

    Haley, you look like the Polly Pocket I wished they made

  • Andrea Raymer

    Haley. I haven’t thought about Rainforest Cafe in YEARS and now you have reminded me that it used to be my favorite restaurant.

    • Haley Nahman

      omg what! lol

  • Imaiya Ravichandran

    The W**dy Al**n shade!!!!! yas.

  • I absolutely adore this – I love Diane Keaton’s outfits in Annie Hall and you are rocking them all. Serious style inspo

    – Natalie

  • You look so good in these outfits!!!!

  • Yvonne Dunlevie

    Haley has actually become Diane in look 2

  • EMS

    Those LL Bean khakis look awesome on you, Haley!!!

  • Sophie

    Gotta shout out to white turtleneck Hamptons Keaton in Something’s Gotta Give!

  • “I actually look like a hostess at an upscale Rainforest Cafe.” Haley. Stop. This is amazing, all of it.

  • grace

    I’ve been anticipating this piece ever since the To Do List piece was published. Doesn’t disappoint!

    • Haley Nahman

      You have good eyes!!!

  • Harling Ross

    “I actually look a hostess at an upscale Rainforest Cafe.” YOU DID IT AGAIN HALEY I AM LAUGHING OUT LOUD

    • Haley Nahman

      ur my best audience harls

    • Teresa

      I was once a hostess at the Rainforest Cafe…true story. You look much better than my uniform ever did.

  • alien princess~

    i support the third look – you may have felt uncomfortable but if you hadn’t mentioned it, i wouldn’t have been able to tell!

  • only because I read the commentary in the article did I end up thinking that these outfits aren’t 100% made for you, because the outfit shots prove otherwise! they all look amazing Haley, you’re definitely pulling them off without the serious grandpa look!

    • Haley Nahman


  • Samantha Lee

    Haha, love this. You are so dead on about her unexplainable unformulaic style. Passing this on to a friend who is a HUGE Annie Hall/Diane Keaton fan.

  • Marley Arviso

    just bought those LL Bean slacks because of this hahaha

    • Haley Nahman

      OMG YES!! hahaha

  • Mercedes Ayala

    the “ahem” was needed and appreciated. and all of these are aamaaazing

  • Oh this is gooood.

  • Katie in black


    Love the outfits Haley, you look so cool <3

  • hilary

    I looooove your shoes in the first two. Where are those from?

    • Haley Nahman

      Oscar de la Renta are the first, Freda Salvador are the second!

  • AryaChic

    haha looks like you had a lot of fun! You did a great job mimicking her outfits


  • Janine

    Diane Keaton’s style has always been perfect. Even when people make fun of what she’s wearing, I think she looks great. And you look fantastic in all of these photos. Especially with the hat and LL Bean pants.
    DK really is an interesting person. She always had this great style and dated some of the most intelligent, attractive, and talented men.

  • Sabah Malik

    “I appear to have just jumped off a very expensive horse.” – BEST

  • Calli

    Need the sources on those MFing dope mules!

    • Krista Anna Lewis

      Oscar de la Renta!

    • Haley Nahman

      Unless you mean the black ones, in which case Freda Salvador!

  • Laura

    You pull it off, but differently, more polished looking. Anyway, I love these looks on both you and Diane Keaton. I was just watching the movie “Interiors” on Amazon Prime today. For anyone interested, It’s a different kind of “Unidentified Dude” film from 1978 that DK did after “Annie Hall”. Anyway, the style choices in that movie – especially the mother and DK’s character – along with the decorating/scenery, is really interesting because all are very prominent and really interweaves with the storyline. One of my all time favorites.

  • Love the 5/6 outfit!

  • Serena

    “Unidentified Man” – you deserve a pulitzer!

  • I think you nailed it,

  • I think I am trying this at home. lol

  • I’m having a moment with your Six-Layer Moment, omg.

  • Diane Keaton’s style is goals. I absolutely loved this post and can’t wait to have my Diane moment. Just got to go raid my dad’s closet for his tweed blazers and eighties ties.

  • I unashamedly love ties. I have some that my dad used to wear but most of them come from Goodwill. I have two Jerry Garcia designed ties for which I paid less than $10 each. (Clearly, the pricer didn’t recognize what they were.) I have a dark red nearly burgundy silky tie with pictures of lizards with red eyes who are lounging on branches. Ties aren’t just lovely; they’re also practical. You’re getting dressed one fine morning and you discover that the chest-level buttons are gapping. You throw on and knot a tie- I prefer the Oriental knot to the Windsor because the ties lies flat- and boom! You’ve got a fashion statement instead of a faux pas.

  • Nicole Depew

    I don’t think she’s wearing a turtleneck in the last picture. It looks like the button down buttoned all the way up with the collar turned up…so you don’t have to be quite as sweaty in this outfit 🙂