Imagine life as a romantic comedy. Strangers would join you in spontaneous dance sequences set to Hall & Oates. Youβd live in an extravagant brownstone apartment, steps away from your closest friends. Hinge dates wouldnβt be awful. You could finally delete all the dating apps because youβd soon reunite with theΒ one who got awayΒ while perusing your local bookstore in the perfect fall outfit. This best friend-turned-soulmate would profess their love at a New Yearβs Eve party, and (surprise!) youβd live happily ever after.
If only the trajectory of our lives could be written by Nora Ephron. Instead, we must settle for realityβi.e., fewer grand gestures and even fewer grand apartments (excuse me while I raise my eyebrows at Jenna Rinkβs massive closet inΒ 13 Going On 30). But all hope isnβt lost. While our ordinary lives may never compare to a screenplay, there is one thing we can all emulate: our favorite rom-com heroineβs fall outfits. After all, thereβs a Meg Ryan in all of us, daydreaming about bouquets of newly sharpened pencils.
Youβve Got Mail
Let us introduce you to Kathleen Kelly, the queen of versatile fall layers. Whether sheβs 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 fromΒ Youβve Got MailΒ is an outright impossible task, thereβs one look thatβll 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.
Pretty Woman
Her on-screen chemistry with Richard Gere is palpable, and her evolving sense of style is a whole mood. When the weather canβt make up its mind between summer and fall, may we suggest channeling Julia Roberts in Pretty Woman? Because letβs face it: You can never go wrong with a short suit. One of Vivianβs 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. Itβll become your go-to outfit on a 65-degree dayβyou know, the days when you canβt decide what to wear for the life of you. Now, youβll be prepared.
Breakfast at Tiffanyβs
Fads, by definition, will always come and go. Whenever youβre 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. Youβll be ready for anything that comes your way, including an impromptu make out session in the rain.
When Harry Met Sally
It wouldnβt be a fall rom-com roundup without mentioningΒ theΒ fall rom-com. Look at thatβMeg 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, we would wear what sheβs wearing.
Crazy Rich Asians
Thereβs so much to love about this movie: the storytelling, the representation, Henry Goldingβs absβand of course, the opulence. Sure, itβs not every day that we can do a Cinderella-esque ball gown. But the red baby doll 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.
Love and Other Drugs
Before Taylor Swift released the 10-minute version ofΒ All Too Well, we were Jake Gyllenhaal fans. And weβll leave it at that because this is about Anne Hathaway and her impeccable style both on and off-screen. InΒ Love and Other Drugs, we canβt 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.
500 Days of Summer
Itβs been 13 years, and we are still not over how anyone could reject the perfection that is Joseph Gordon-Levitt. We get it, itβs 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.