How to Dress Like Sally Albright in When Harry Met Sally

How To Dress Like Your Novel is a series in which we explore what Creative Director Raquel calls “the pursuit of literary aesthetic coordination.” In this edition, we turn away from the novel and, instead, towards an iconic film character from one of our favorite writers – Nora Ephron’s Sally Albright. Culture Editor Eliza Campbell tackles all things When Harry Met Sally and creates outfits that Sally would love to wear in 2019.

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If they asked me, I could write a book about how much I adore the costume design in When Harry Met Sally. (Praise Gloria Gresham, costume designer extraordinaire.) The film itself is a personal favourite of mine and a colossus bestriding the romantic comedy genre. You get the sense that every rom-com that came after merely tries to capture the magic in this film (Richard Curtis definitely owes a lot of his career to the screenwriting talent of Nora Ephron). Ultimately, When Harry Met Sally is a love letter to New York, love, friendship, and figuring it all out. Swept up in crackling dialogue and a big band soundtrack, it also has some of the most consistently excellent clothes in any of the rom-coms that came before or after. The film was released in 1989 and the story takes us all the way through this tacky, weird, Reagan-era, stock market booming decade that is currently being mined for ideas and nostalgia profit by fashion executives. Sally’s style is congruous with the style of the decade but it’s quirkier, a little woollen and academic that adapts with her age and place in life. I’m going to try and capture some of that styling magic in 2019. Warning: contains jumpers.

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ONE: OKLAHOMA KARAOKE

Film still from When Harry Met Sally (1994).

This might not be the first outfit you think of when you think of When Harry met Sally but I absolutely love it. It’s a clever little twist because Harry just wore the same outfit in a previous scene when they’re laying down a rug in his apartment— soul mates even down to their white turtleneck sweaters. Sally’s more feminine version has her top tucked into high-waisted jeans with a belt to accent the waist and a cross-body bag. And Other Stories sell this really lovely Alpaca Blend Turtleneck Sweater, but it’s a little pricey for that pure white material that would absolutely get dirty the second I started wearing it. On the cheaper side, Monki have this lovely chunky knit sweater. High-waisted blue jeans are easy to come by but I really love the addition of the black belt here to give it a bit more shape. You can go simple or jazz it up with these two slightly decorative buckles from Mango here and here.

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TWO: MARIE AND JESS’ WEDDING RECEPTION

Still from When Harry Met Sally (1994).

Green dresses always stick out for me because Atonement (2007) was a deeply formative viewing experience. I love this one in particular for its 80s weirdness, including the horrible shoulder pads and odd hem line. It’s a definite nod to prom and this scene’s argument between Harry and Sally in the kitchen is definitely teen-worthy. It’s another clever bit of styling to show Sally’s emotions and behaviour through her clothing. Unfortunately, it’s such a unique dress there’s nothing really like it on the market and to be honest, as great as it is, I do think it’s best left in this 80s time capsule. However, I love green dresses and I can recommend a few. Reformation is horrifyingly expensive but they do dresses well. You can resolve to invest or to just cry onto your laptop screen. I love this midi wrap dress with ruffled sleeves and this dress with a sweetheart neckline and puff sleeves. On the cheaper end of things there’s this on-sale Faithfull midi dress with ruffle sleeves via ASOS and this Mango pleated dress.

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THREE: ‘SOMEONE IS STARING AT YOU IN PERSONAL GROWTH’

Still from When Harry Met Sally (1994).

This is my personal favourite outfit that Sally wears throughout the film. It’s a little more relaxed than the previous two times we’ve seen her (in a formal blouse and bad hair on the plane, and later announcing her break-up with Joe in a string of pearls and shoulder-padded jacket). Sally meets Harry for the third time in a brown corduroy jacket, a red turtleneck jumper underneath and blue jeans with a large pair of staggeringly 80s glasses on a string. It’s weird and academic, and I love it. You get the sense that Gloria Gresham is trying to convey that Sally has wound down from her break-up and is choosing comfort (personally and sartorially) over structured outfits and relationships. Anyway, I like that interpretation. And Other Stories have this lovely blazer in rust that’s currently on sale (and has matching trousers, might I add). If corduroy isn’t your thing (which hurts me a little, I have to say) you might get on better with this oversized blazer from Monki in either brown plaid or grey. For the red turtleneck jumper And Other Stories has a gorgeous oversized mock neck sweater in burgundy.  

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I also have a few special sartorial mentions. I’m a big fan of Sally’s big brown wrap coat that she wears on the double date with Harry, Jess, and Marie. It’s elegant and makes Meg Ryan look a thousand feet tall next to tiny Carrie Fisher. 

I’m also a big fan of the way she pairs the red cable knit jumper from the bookstore scene with a black skirt and tights later in the film. I don’t have much to say about it, it’s just a great look. Perfect for autumn.

Finally, I feel like I have to mention the grey bowler hat because it’s iconic and I hate it so much I love it. Plus, it furthers my theory that as Sally gets used to her split from Joe she chooses to wear kookier and more relaxed outfits. It’s a little Diane Keaton in Annie Hall (1978) – which is a great outfit in a terrible film by a revolting man – and you get the sense that Gresham is trying to bring some 70s costuming magic to Sally as she tries dating again.

I hope you can hear the big band soundtrack swelling as you run through the night on New Year’s Eve to tell a girl you met 12 years ago just how much you love her. If not, I hope you’re content with an image of autumn leaves falling under a gloomy New York City sky as you wander around in various great outfits. Before I leave you, here are a few outfits that I’ve put together from my own wardrobe that have a Sally Albright vibe.

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Eliza Campbell is Culture Editor of the Attic on Eighth. When she’s not reading, writing, or in a rehearsal room, she loves to sit in galleries, libraries, and coffee shops listening to period drama soundtracks and watching the world go by.