7 Fall Outfits Inspired by Our Favorite Rom-Coms

Imagine life as a romantic comedy. Strangers would join you in spontaneous dance sequences set to Hall & Oates. You’d live in an extravagant brownstone apartment, steps away from your closest friends. Hinge dates wouldn’t be awful. In fact, you could finally delete all the dating apps, because you’d soon reunite with the one who got away while perusing your local bookstore in the perfect fall outfit. This best friend-turned-soulmate would profess their love at a New Year’s Eve party, and (surprise!) you’d live happily ever after.

If only the trajectory of our lives could be written by Nora Ephron. Instead, we must settle for reality—i.e. less grand gestures and even less grand apartments (excuse me while I raise my eyebrows at Jenna Rink’s massive closet in 13 Going On 30). But all hope isn’t lost. While our ordinary lives may never compare to a screenplay, there is one thing we can all emulate: our favorite rom-com heroine’s fall outfits. After all, there’s a Meg Ryan in all of us, daydreaming about bouquets of newly-sharpened pencils.

1. You’ve Got Mail

Source: Warner Bros.

Let me introduce you to Kathleen Kelly, the queen of versatile fall layers. Whether she’s ambling about New York City or emailing NY152 from her perfectly imperfect Upper West Side apartment, she somehow manages to look both timeless and effortless in every single scene.

While choosing the best outfit from You’ve Got Mail is an outright impossible task, there’s one look that’ll always work (in 1998 and 2022): a long-sleeve bodysuit under a jumper dress. Kathleen completes the ensemble with tights, loafers, and, later on, a chunky coat and scarf. These layers upon layers of muted neutrals are a fail-proof way to dress this fall.

bodysuit | bodysuit (plus-size) | dress | dress (plus-size) | loafers | bag

2. Pretty Woman

Source: Touchstone Pictures

Her on-screen chemistry with Richard Gere is palpable, and her evolving sense of style is a whole mood. When the weather can’t make up its mind between summer and fall, may I suggest channeling Julia Roberts in Pretty Woman? Because let’s face it: You can never go wrong with a short suit. One of Vivian’s slightly more understated (but trendy as ever) fashion moments deserves a place in your closet.

To 2022-ify it, keep the monochrome look going with a cropped blazer and matching jeans. It’ll become your go-to outfit on a 65-degree day—you know, the days when you can’t decide what to wear for the life of you. Now, you’ll be prepared.

blazer | cropped button-up | jeans | mules

3. Breakfast at Tiffany’s

Source: Paramount Pictures

Fads, by definition, will always come and go. Whenever you’re not sure what to wear, revert to the classics. Pull an Audrey Hepburn and Golightly on the accessories with a statement trench coat and hair scarf. You’ll be ready for anything that comes your way, including an impromptu makeout session in the rain.

trench coat | dress | slingbacks | sunglasses

4. When Harry Met Sally

Source: Columbia Pictures

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

sweater | sweater (plus-size) | skirt | skirt (plus-size) | tights | loafers

5. Crazy Rich Asians

Source: Warner Bros. Pictures

There’s so much to love about this movie: the storytelling, the representation, Henry Golding’s abs—and of course, the opulence. Sure, it’s not every day that we can don a Cinderella-esque ball gown. But the red babydoll dress Rachel wears while spending the day with her friend feels a tad more attainable. Slingback pumps and a trench will make this dressier look suitable for any occasion.

dress | dress (plus-size) | trench coat | trench coat (plus-size) | shoes | bag

6. Love and Other Drugs

Source: 20th Century Studios

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.

cable-knit sweater | sweater (plus-size) | jeans | jeans (plus-size) | watch

7. 500 Days of Summer

Source: Searchlight Pictures

It’s been 13 years, and I’m still not over how anyone could reject the perfection that is Joseph Gordon-Levitt. I get it, it’s a story about love, not a love story. Such a refreshing take. Whatever. But Summer redeems herself with her romantic and retro style. Feeling blue (like Tom)? Go for a vintage blouse and a-line denim skirt.

top | top (plus-size) | skirt | skirt (plus-size) | flats