6 Fall Outfits Inspired by Our Favorite Rom-Coms

Imagine if our lives were a romantic comedy. We’d live in a fabulous apartment in the city, steps away from everyone we know. Our main love interest would excel at all forms of witty banter. In fact, we could finally delete the dating apps, because this friend-turned-soulmate would profess their love for us at a New Year’s Eve party, and happily ever after we’d live.

Unfortunately, neither of us are the main character in a Nora Ephron film. Instead, we must settle for reality and regular-sized apartments (looking at you, 30-year old Jenna Rink)—but all hope isn’t lost. While our ordinary lives may never compare to a movie script, we can always look the part of a rom-com heroine. This fall, we’re recreating our favorite on-screen outfits—and manifesting our very own Tom Hanks.


1. You’ve Got Mail

Source: Warner Bros. Pictures

loafers | bag | sweater vest | button-up (plus) | jeans (curve)

If I could insert myself into any fictional world it would be the world of You’ve Got Mail. I’d have an Upper West Side address and own a children’s bookstore, and would be falling in love on AOL rather than doomscrolling on TikTok. But for now, I’ll take any one of Kathleen Kelly’s charming, understated outfits. Copy her scholarly look with a white button-down, sweater vest, jeans, and loafers. Welcome to Meg Ryan Fall.


2. Emily in Paris

Source: Netflix


jacket | tank | scarf | skirt (plus)| shoes

Emily makes everything look easy, from living in a foreign country without speaking the language, to mixing three types of plaid and somehow pulling it off. What can’t she do? One of her most memorable looks was this kelly green number, which happens to scream fall. Then all you’ll need is a neck scarf, a baguette, and maybe a Duolingo subscription.


3. Crazy Rich Asians

Source: Warner Bros. Pictures

slingbacks | bag | trench coat | earrings | dress (plus)

There’s so much to love about this movie: the outfits, the opulence, Henry Golding’s abs. Sure, it’s not every day that we can don a Cinderella-esque ball gown, but this red babydoll dress feels a tad more attainable. Complete the look with Mary Jane heels and a trench coat, and you’ll be ready for your next fall date night.


4. Love and Other Drugs

Source: 20th Century Studios

clogs | socks | sweater (plus)| bag | jeans (plus)

Before Taylor Swift released the 10-minute version of All Too Well, I was a Jake Gyllenhaal fan. And I’ll leave it at that because this is about Anne Hathaway and her impeccable style both on and off-screen. In Love and Other Drugs, we can’t help but fall for her free-spirited nature and effortless outfits, like the overalls and camel coat that appear throughout the film. For those days you plan to stay inside your sprawling, industrial-style loft, we suggest opting for a cozy cable-knit sweater and relaxed-fit jeans.


5. When Harry Met Sally

Source: Columbia Pictures


ballet flats | sweater (plus) | hoops | tights | skirt (plus)

It wouldn’t be a fall rom-com roundup without mentioning the fall rom-com. Look at that—Meg Ryan does it again. How dare she be this consistently fashionable? While her Central Park outfit (the one with the bowler hat) might be her most iconic, this red sweater and skirt combo is a classic worth repeating. I’ll wear what she’s wearing.


6. 500 Days of Summer

Source: Searchlight Pictures

boots | sweater (plus)| skirt (plus) | bag

This “story about love” flipped every rom-com trope on its head. But while it had a modern take on the meaning of happily ever afters, the fashion was as vintage as ever. If you’re still living in 2009 like I am, then you’ve been tempted to copy Summer’s entire quirky, blue-hued wardrobe. Her romantic, retro style is extremely Pinterest worthy, and since denim skirts are back in full force this year, it’s 2023 worthy as well. To make yours feel a little more wearable, pair it with a basic sweater and boots.


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