6 Fall Outfits I’m Stealing From ‘When Harry Met Sally’

I love any and all Meg Ryan/Nora Ephron joint ventures as much as the next sane person, but When Harry Met Sally is my absolute favorite. I have watched it no less than 12 times, the twelfth being when I recently learned that my boyfriend had never seen it before and I sought to correct that immediately.

Ten minutes into the movie, I realized I wasn’t really paying attention to the plot. I didn’t need to — I could recite the movie start to finish. I was, however, paying extremely close attention to Meg Ryan’s outfits. I’ve admired them before, obviously, but during this particular viewing session they were all I could think about, perhaps because When Harry Met Sally is a goddamn beautiful onion with endless layers to unpack, or perhaps because fall weather is around the corner and Meg’s outfits are autumnal style porn.

Below are six I plan to copy as soon as the tree outside my window turns orange:

Knee socks, khaki Bermuda shorts, a button down and a cardigan is pretty much the perfect outfit for transitional temperatures. My evidence for this assertion stems from the fact that my knees are the only part of my body that don’t seem to freak out when confronted with a chilly breeze. My arms and cheeks and inner thighs and toes, on the other hand, are wimps.

A gray plaid blazer is a fall staple I have yet to acquire, but rest assured it is now at the top of my list. I am also planning to button all buttons right up to my throat, which I will wrap like a gift to the world with a silky scarf. I’m on the fence about mauve nail polish, but let’s touch base again in November.

My mother recently gave me a pair of stiff, dark blue Levi’s that she wore in the ’80s. They reach all the way to my diaphragm and make me look like a bird watcher and I love them with all my heart but until now haven’t been able to figure out what to wear with them. Lo and behold, the answer is simpler than a piece of apple pie a la mode, heated, with strawberry ice cream on the side (that’s a When Harry Met Sally reference for all my fellow freaks out there): a thick white turtleneck and a brown belt.

Just when I was about to relinquish ankle boots to the trend graveyard, this outfit swooped in and re-calibrated my imagination. I’m going to be tucking them under my mom jeans right and left, just you wait. Also, I think I need a messenger bag? TBD.

I love this outfit because Sally wears it in the scene immediately after Harry tells her, “I think you should wear skirts more. You look really good in skirts.” AND SHE DOES. She also proves again and again that you don’t have to overcomplicate an outfit (a definite tendency of mine) for it to resonate. I’m stowing “black mini skirt and cozy red sweater” in the back pocket of my brain as a chic, easy ensemble option for days this fall when I have no idea what to wear but really want to look like a Jil Sander ad.

Last but not least, this outfit inspired the very important revelation that bowler hats are the fall equivalent of bucket hats and I am planning to incorporate one into my wardrobe posthaste.

Now it’s your turn: Do you have a favorite movie or TV show with ample style fodder? I’ve got winter covered thanks to Love Story, but I’m in the market for spring and summer inspiration.

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  • Emilie Hill-Smith

    I literally went on man repeller today to decide what my perfect fall outfit would be today, this is everything I wanted and more, thank you

    • Harling Ross


  • Monica Tiffany

    Daryl Hannah’s clothes in Roxanne. The hiking boots. Granny glasses. Denim & flannel & floral. Dream.

    • Alexa M


  • Fiona Foran

    This is truth. And I will always have a love for that blouse with the embroidery below the collar, and the cable v-neck (or maybe cardie?) look that Sally wore in the diner scene.

  • Julia

    When Harry Met Sally is one of my favs and now I have an excuse to watch it again

  • Autumn

    Yes bring back the bowler hat!!
    Also, can we please talk about the style on Golden Girls?! It’s the most amazing, opposite-of-menocore style on a tv show

  • CarlyC

    I got really excited when I saw the red honey roll-neck wool sweater, then got really sad when I clicked the link and saw the price. *Sigh* It’s so beautiful.

  • Dulce Partida

    Thank you! I’m also gonna do it! Now I will have to wait for December and January (that’s when is cold where I live)…

    • Engels_Beard

      Totally with you. It was 92 degrees here….

  • olivia

    I’ve seen this movie 10 times and never noticed the skirt thing!! I also love the hair in movies from before hair straighteners were a thing! Good curly hair inspo

    • Jade

      It was just the opposite: back then if you didn’t already have curly hair, you had to get a perm.

  • Chelsea White

    I watch When Harry Met Sally regularly (like at least once or twice a month), I have always wanted to re-create Sally’s outfits!! Thanks for the inspo!

  • Kasia Chmara

    I love this style 🙂

  • Jo

    One of my very favourite films! Always loved Sally’s style and think Harry looks so much hotter with the beard!

  • Summer is always Dirty Dancing!

  • Chloe

    I think I’ve probably watched this 30+ times. I can recite the whole thing by heart. I’m now onto “You’ve Got Mail” – another great autumnal Nora Ephron/Meg Ryan powerhouse. “Don’t you love New York in the fall? It makes me want to buy school supplies. I would send you a bouquet of newly sharpened pencils if I knew your name & address.”

    Anyways: I have toiled over this for many viewings but – the black skirt that she wears when they are unfurling the rug & discussing Harry’s bad date – are those culottes or a skirt? Yes, I know that this scene comes right after the “you should wear more skirts” comment, but I am 80% sure that they are culottes. Despite my rewinding & rewatching, I’m still not confident in that sartorial observation but, culottes with tights are perhaps even a better fall staple than a skirt and tights.

    • Abby

      YES You’ve Got Mail is one of my all time faves

    • Maggie Lanham

      AGHHH YES. When Harry Met Sally is my current any-mood movie and You’ve Got Mail was when I was younger. There’s such a small fire in both of those characters that I just absolutely love. And the scene where she tells off Billy Crystal because “she will make love when it is making love! not like you do it, like you’re out for revenge or something” SO resonates right now. She just claps back with the perfect response for a male’s shaming. I LOVE THIS MOVIE.

      • Chloe

        Her characters in both of those movies are SO relatable. Mostly thanks to Nora Ephron’s writing, she plays such a dynamic character in both. It’s hard to find a character like her in movies today – today, everyone is trying too hard to be the perfect woman, the perfect feminist, the perfect businesswoman, the perfect love interest, etc. It’s so inauthentic. Sally was balanced & believable.

        • Maggie Lanham

          Totally agreed – Nora really knew how to write a whole, real woman.

          • gracesface

            Heartburn really overwhelmed me but Meryl Streep was really great and Nora wrote such an honest women.

          • Kelsey


          • Basil

            YES! I recently decided to watch Sleepless in Seattle again for the first time in years, wanting something a bit brainless and came away thinking that it was just so gooood and funny. Incredibly funny

          • Martine

            You actually know people who act like that? I sure don’t. But then, most women I know wouldn’t date a short guy with Jewish sense of humor( absolutely no insult or disrespect to the religion intended.)

    • Shawn

      The “school supplies” line kills me EVERY TIME.

    • Janine

      I’ve probably seen the movie 10,000 times; I think they were dark shorts. That was big in the ’80s. Tights under shorts. I remember wearing them. Speak of cling-y – especially if the shorts were lined. 😕

    • Janine

      Oh. One great line from WHMS: “Someone is staring at you in Personal Growth.”

    • Lisa Zahn

      I just watched the movie. They were definitely culottes or shorts with wide-ish legs.

      • Chloe

        Ahhhh – thank you!

  • Annabel Flores

    Cher in The Witches of Eastwick!

  • Hayls

    I JUST saw this movie for the first time a week ago – and the whole time I was thinking, 1. How did I get this far in life without seeing this, it’s amazing and 2. I love literally ALL of her outfits, and I need a gray plaid blazer in my life immediately

  • Lindsey

    Just re-watched this two weeks ago and felt the same way! “Damn, Sally’s clothes are on point in this movie….” *especially* (to me) that very Annie Hall outfit of hers you pointed out at the end. It’s so good.

    • tinygoldenpins

      It is sad to say that “Annie Hall” is still one of my style movies. When she is wearing the plaid shirt and a grandfather cardigan over it….I think it’s the breaking up scene when they discuss their books.

      • Lindsey

        Not sad at all! Annie Hall is classic for a reason! All her looks are iconic.

  • Emily

    yes, the style in this movie is so amazing!! her glasses, like in the bookstore scene, are also on point.

  • Vanessa Gentile

    does anyone else feel like Haley Nahman IS Sally/Meg Ryan ?!?!?!?!?

  • Megan

    i have never clicked a link so fast in my life
    i have been getting so excited about WHMS watching season and now to dress the part too! dreamy

    • cryptdang

      I love this–I totally watch movies seasonally too! (And this movie is definitely on my Fall list!)

  • Maria Fernandez-Davila

    omg I love this movie so much and now feel an immediate need to watch this over the weekend. Now if only NYC would give us actual fall weather to test out these amazing outfits…..

  • tinygoldenpins

    The bad news is: after being done with the 80s and 90s, I never wanted to see anything from those decades again; the good news is: I have all of these clothes in my closet (skipping the khaki shorts, knee socks for obvious reasons — I was there the first time around).

    • Jade

      This was my first thought: we have to wear these styles AGAIN?

  • Cate

    Mary in the Mary Tyler Moore Show !

  • Jessie Erikson

    you have the best hair to dress like her too!!! a few years ago, I saw a bridesmaid dress JUST like the one she wore at jess & marie’s wedding, and I really wanted to wear it for halloween, but I thought no one would know what I was doing, at all.

    it’s funny though – I have rarely thought about her outfits much, but I have thought about all her different hairstyles a LOT. my sister and i have often discussed favorites (hers is the ringlets toward the end; I think mine is either airport sally or I-feel-fine-about-the-breakup sally). as for her clothes, she definitely makes me want to wear turtlenecks.

    I am also someone who has watched this a million times… I typically tell people this is just my favorite movie, in general. my sister’s old VHS tape even had deleted scenes, and they were good. apparently alice’s whole life was originally a bigger thing??? wish we had gotten to know alice better.

  • Maria

    One of my favorites!! also we don’t get Fall weather in Miami so I’m living vicariously through this article lol

  • M Rae

    please take a peek at ‘witches of eastwick’ (currently avail ondemand in middle America). I came for the weird 80s Halloween vibes, but 100% stayed for the outfits. I paused to further inspect SO many times.

  • eva

    style inspo always forever? desperately seaching susan…sometimes i’m a susan sometimes i’m a roberta, but not once since 1985 have i not PINED for the clothes in this film!

    • sdanorth

      One of my biggest regrets in life is not getting the boots when they had them at Wild Pair!

  • One of my faves of all time. If you can believe it, once many years ago, someone told me this film was “boring” and they couldn’t understand why I liked it. I could not in good conscience, remain ‘friends’ or even acquaintances with this individual. Who doesn’t LOVE When Harry Met Sally? Classic! Thanks for pointing out the classic wardrobe as well.

  • gracesface

    Omg yes, LOVE STORY!!!! And I love watching the show Thirtysomething, the fashion is NUTS and soooo 90s. The character Melissa has the most amazing coat I’ve ever seen.


    • Lisa Zahn

      Yes! Hope was my idol in so many ways back in the ’90s. I WAS Hope. 🙂

      • gracesface

        I’d like to be Ellyn, please!! (but really I’m married to a Gary).

  • Maren Douglas

    I watched this movie last night and thought to myself how great a MR article would be on it… was not disappointed. Couldn’t love this movie more!!

  • Christine Dyson

    Currently, I am unexpectedly loving Jane Fonda’s style in Klute. I wasn’t a fan of 70s style as a kid at the time, I was obsessed with 50s style from a weekly diet of watching old movies every Saturday on BBC2 (we only had 3 channels.. crazy I know!) but 40 years on I am finally quite taken with it! Also have always been obsessed with Julie Christie’s style in Billy Liar x

  • Rebecca MacDougall

    I literally wrote a blog post about how much I love Sallys outfits and never posted it. This is way better than anything I could write!

  • Suzan

    Yes to all these looks!
    And I’m down with her nailpolish too! I think you choose one a bit too mauve-y though, it needs to be a tad more pinkish, judging from that still. I have Sally Hansens So Much Fawn, which looks like it comes very close colourwise and is very wearable for a lot of skintones (unlike mauve), so I’d recommend that one, Harling!

  • One of my all time favorite movies!!

  • Sheila Callahan

    As a “woman of a certain age” who believes that classic pieces of good quality never go out of style, I was pleased to see the positive response to this article. With the exception of the hat (have yet to find a hat that’s flattering), I own all of these pieces and wear them regularly as weather permits. While, IMHO, today’s trends scream “look at me!” these pieces turn heads with their “why didn’t I think of that?” simplicity.

    • Lisa Zahn

      Yes! I’m so with you. We just weren’t trying to so hard in the 90s. The outfits were simple, comfortable, and appropriate for the weather/occasion most of the time. But I read articles like this, in which young people are adopting the fashions of “my day” and wonder if they’re being serious or ironic though? I’m never quite sure…

      • Sheila Callahan

        I think they’ll probably tire of it and move on to something else that’s “new” – until they get to be our age …

  • Harriet Eliza-Blue Idle

    my God it’s like this article was written especially for me

  • All great looks, but the first thing I noticed was Billy Crystal’s jeans…

  • Olivia Kohlstaedt

    I’ll have what she’s having.

    The Emma Thompson version of “Much Ado About Nothing” is not so much my summer style inspiration, but my summer VIBE inspiration. I try to dress in a way that makes me feel like I’m a character in that movie, reciting poems in a tree and consuming all the grapes and cheese.

    • Ariana

      Christ, YES!! All the billowy fabric and pithy comebacks. I also like the floral frocks in Joss Whedon’s version of the same…

  • Amanda Montgomery

    Oh my god Harling this is my favorite article of the fall thus far. The silk scarf and the bucket hat have stood out in my memory since childhood, but I could never put my finger on them. Best believe I will be purchasing these and wearing them like a second skin this fall.

  • Oriana

    Everything you said + Harry´s apartment (amazing windows and view).

  • Never watched this movie! Idk why, just never jumped out at me. I got I got some work to do! 🙂

    • Hannah Johnson

      Same!!! 🙂 Maybe I’ll watch it tonight!

  • Kate

    Summer = Stealing Beauty.

  • Shawn

    God bless you, woman. This is the tribute that Nora and Sally deserve.

  • Janine

    Definitely The Talented Mr. Ripley for summer.

  • Shereen Fischer

    At some point can we revisit Marissa Tomei in Only You? I want soooo many of those lovelies in my closet.

  • Kristina Burkey

    You didn’t need to point out the pie order is a line from the movie. It could have just been a private moment savored between the fans. Noobs are on their own. 😀

  • Basil

    Borg vs McEnroe made me want to run out and buy sports wear.
    This outfit is pretty much my A/W wardrobe sorted forever https://uploads.disquscdn.com/images/6306c094c515f694a14928c9e42a96019fffd0f489cf06f7350af7a07eb2be92.jpg

  • Silvana Flora

    Cate Blanchette’s outifit in 2015 James Vanderbilt’ movie “TRUTH” are wonderful…..does anybody knows who made those silk shirts ?

  • Emmie

    baby fish mouth sweeps the nation

    • cindy

      draw something resembling ANYTHING! hahahahahaha! love that scene!

  • Janine

    Desperately Seeking Susan (you had to be around in the time period to appreciate it; some people hate this movie), Great Expectations, Love Story, Seven, Lost in Translation, Shampoo, Darling, I loved La La Land (costume design was perfection), Unzipped. The list is endless.

  • alexia

    Love this film 🙂 Another one popped into my mind for spring / summer : american gigolo (+ richard gere was just …). Have to watch those two again!

  • Analog House

    My style icon is Blair from “The Facts of Life”.


  • Fayla Garcia

    Yessss! I love When Harry Met Sally!! My day is made.

  • Isabelle McLeod

    Elle Fanning in 20th Century Women!!!!!!! @harling_ross:disqus 🙂

  • Keri Phelan Gagnon

    Karen Allen in “Raiders of the Lost Ark” has the best summer / hot weather / vacation wear throughout the movie. I mean, THIS:


  • Ines Vilares

    Lovely outfits! Definitely great inspiration!

  • Bernadette Lurch

    Thomas Crown Affair…. Rene Russo wears the most sumptuous and sexy fall outfits all throughout.

  • streats

    I’m a huge fan of style on screen pieces like this. 90s and early 2000s shows and movies are sooo ripe for this. I’ll always be a SATC fan no matter what, and at every rewatch I spot new outfits I like, or form new opinions about ones I didn’t care for before.

    Buffy is another great one. Always makes me reconsider leather blazers as a viable jacket option.

    Speaking of leather jackets, Christina Yang in the early seasons of Grey’s Anatomy makes me want to own leather moto jackets in every single colour. There’s also an incredible purple satin sheath dress she wears out to dinner with Burke which I NEEDED in my life and then eventually FOUND. It didn’t quite look as good on me as it did her but I loved it.

    Also a reminder of the wonder that is Phoebe Buffay https://www.manrepeller.com/2016/02/phoebe-buffay-style.html