When Harry Met Sally and Gilmore Girls Both Agree on This Fall Trend

Every time the first leaf drops at the start of fall, fashion people everywhere turn to their favorite on-screen moments to commemorate the new season. Two of the biggest players include When Harry Met Sally and Gilmore Girls. I've heard so many friends talk about the wardrobe inspiration that has come from watching these two pieces of media, and I am right there with them.

One item that has been a major motif between the movie and the show is the argyle sweater. Sally wore hers in Central Park on a walk with Harry, and both Rory and Lorelai Gilmore had multiple sightings in this fall staple. If you're a fan of the New England prep-school vibe, this one is most definitely for you. You won't regret enjoying this roundup.

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On the fashion set:
(Image credit: @emmanuellek_)

If you're looking for a modern-day When Harry Met Sally moment this is it. Harry and Sally would both approve of the primary color scheme and a good blazer.

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(Image credit: @chasemarieee)

An argyle sweater is a perfect piece for layering, so I feel like copying this "too cool for school" look. It feels like an adult take on one of the classic school uniforms I've seen in my favorite TV shows and films.

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(Image credit: @cocobassey)

This photo has convinced me that cozy nights in require this staple.

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On the fictional set:
(Image credit: When Harry Met Sally)

If you like preppy New England fall fashion, then you already know that When Harry Met Sally is the movie to watch. Both Sally and Harry were fond of an argyle sweater-vest throughout the film.

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(Image credit: Gilmore Girls)

Another New England fall favorite happens to be Gilmore Girls, which I just found out takes place in Connecticut. A long list of chunky sweaters layered atop oxford shirts outfitted the cast of characters, and this one was my favorite.

Shop the trend:

Up Next: Welcome to Sweater Season—5 Trends That Are Out and 5 That Are In

Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.