How To Dress Like A Nora Ephron Character

The ‘90s are back.

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sleepless in seattle
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Nora Ephron, film legend and adored essayist, understood main character energy at the height of the ‘90s. Her two most iconic movies are the ultimate argument for complicated relationships in the complicated city she adores, New York: When Harry Met Sally and You’ve Got Mail. Her character’s dressed in a way that was headstrong yet simple — a reflection of Ephron, who wrote many essays exploring her own relationship to fashion. While a black turtleneck or an oversized button-down are timeless basics, thanks to Ephron, they became iconic ‘90s fashion trends, part of the minimalist, classic aesthetic perfected also by celebs like Carolyn Bessette Kennedy and Gwyneth Paltrow along with designers like Calvin Klein and Miuccia Prada.

The world the writer creates on screen is as mesmerizing as the Upper West Side she immortalizes in her essays. There’s a quirkiness to her characters, a human frailty that’s refreshing in the cookie-cutter world of rom-coms. The dialogue’s quick, but equally as human, and easy to imagine overhearing on the street, like, “I don't want an answer. I just want to send this cosmic question out into the void," from You’ve Got Mail. Considering the costuming in Ephron’s films is like considering the writer’s wardrobe herself. There’s an intentionality to the simplicity, one that allows the writing to claim center stage.

Ephron’s characters embody a certain connection to their outfits and the moment those ensembles punctuate in their own lives — Meg Ryan’s breakup jaunt in an oversized blazer in You’ve Got Mail, or the same actor’s frantic tell-all phone call in a rumpled pajama set from When Harry Met Sally, the off-the-shoulder number that witnessed an inevitable “I love you” at the end of the same film. Clothes tell the story before the character has the chance to, making rewatching Ephron’s greatest hits a seasonal ritual not only for their clever lines, but for every of-the-moment ‘90s outfit inspiration.

Ahead, a look at six of the essential pieces inspired by Nora Ephron’s female leads that fit into any fall wardrobe — on the Upper West Side or elsewhere.

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Interior shots of characters’ suspiciously sprawling apartments are among the most iconic in the Nora Ephron universe. They’re not tidy, they’re lived in — with piles of books and mismatched pillows. A signature scene is a shot of the female lead in her bed on the phone. In Sleepless in Seattle, Meg Ryan jumps out of bed when her friend calls to let her know Tom Hanks’ son is on the radio putting out a request for her to dial in. In Julie and Julia, it’s the scene where Amy Adams opens a Julia Childs book for the first time. In Lucky Numbers, Lisa Kudrow plots John Travolta’s lotto win. The look celebrates the intimacy in the mundane routine of life at home, something perhaps even more relatable in 2021. Invest in a smart pajama set just in time for long nights at home. Your iPhone will have to do in place of a landline.

Unapologetic Menswear

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When Harry Met Sally is a masterclass on tailored menswear for women. The lead, Meg Ryan as Sally Albright, navigates a film that’s essentially two hours of her male counterpart explaining men and women’s inability to be friends. Albert Wolsky, the film’s costume designer punctuated the film with men’s pieces reinterpreted for Albright including a bowler hat paired with a leather crossbody bag, and the red sweater and brown suede jacket look at the bookstore. The thing that sets these outfits apart is that they’re worn with irreverent ease —a bit more fitted than the modern trend’s take, but the result is just as cool, if not a little more lived in.

Black Turtlenecks

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In I Feel Bad About My Neck: And Other Thoughts on Being a Woman, Ephron writes extensively about her love for turtlenecks, black turtlenecks, specifically. “Everything matches black, especially black,” she writes. “Sometimes I buy something that isn’t black, and I put it on and I am so sorry,” she adds later. Black turtlenecks get the screen time they deserve on Ephron’s practically minded leads (like Meg Ryan’s character, Kathleen Kelly, in You’ve Got Mail). Since it’s perpetually autumn in the world of Nora Ephron, turtlenecks are seen on their own or layered under dresses, but their simplicity serves as a grounding force for her heroines.

Small Watches

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Accessories are low profile in Ephron movies. Female leads carry mostly shoulder or crossbody bags, and there are no designer labels to be found. Ephron herself was known for her distaste of the accessory based on the 2002 essay, "I Hate My Purse," which she included in her literary compilation, I Feel Bad About My Neck: And Other Thoughts on Being a Woman. She evangelizes against the oppression of a heavy purse in a world where essentials can really just fit in a pocket. But an accessory the ever-practical Ephron can get behind is a watch. Almost every female lead sports a sleek timepiece. They’re usually small and worn tight to the wrist. There’s something charming and matter-of-fact about a watch, especially in a digital age.

Chunky Sweaters

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Another iconic When Harry Met Sally moment, involving a rug and an empty apartment, is borderline distracting to watch because of the two leads’ (Billy Crystal plays Harry) knit sweaters. Harry outshines Sally sartorially for the first time in the film wearing a fisherman-style crewneck with a dropped shoulder. And in Bewitched, a chunky knit is part of Nicole Kidman’s stylish uniform. The inspiration for the iconic line of questioning from You’ve Got Mail, “Don’t you love New York in the fall?” feels entirely apropos in a world of cozy sweaters and day dates at the Met. Styled with only blue jeans and the vintage accessory of a plastic, disposable water bottle, the look couldn’t be simpler. Read as: easier to copy.

Anything But Mini Skirts


Ephron characters are known to don a below-the-knee skirt look for both a run to Zabar’s and a breakup uptown alike. Long skirts are a ‘90s staple that have seen a modern resurgence. Take a page out of Kathleen Kelly’s look in You’ve Got Mail by pairing a skirt with ballet flats or boots and matching tights. The look feels cool in an I-have-better-things-to-worry-about-than-what’s-on-trend kind of way, which just might be the embodiment of what makes Ephron and her characters so evergreen.

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