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Fall outfits, pumpkin candles, chai tea lattes, a reason to believe in love (even if it’s only for an hour and 58 minutes). Fall isn’t just the season of new beginnings and sweater vests, it’s also the season of rom-coms, which is why I’ll now be watching You’ve Got Mail on repeat while dreaming about bouquets of newly-sharpened pencils.
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I could write a thesis about romantic comedies that take place between the months of September and November, but as much as I fall for the grand gestures and predictable storylines, it’s the fashion that wins me over again and again. Those too-good-to-be-true endings may not always happen in real life—but the outfits can.
1. You’ve Got Mail
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 2021): a mock neck 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.
dress / dress (plus-size) / long-sleeve shirt / long-sleeve shirt (plus-size) / bag / tights / loafers
2. Pretty Woman
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.
The oversized blazer and matching bermuda shorts will be 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.
suit set / white button-up / belt / mules
3. Breakfast at Tiffany’s
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 / hair scarf / cat-eye sunglasses / shoes
4. 500 Days of Summer
This “story about love” broke almost every single rom-com trope (and had us replaying its soundtrack for all of 2009). But while it had a modern take on the meaning of “happily ever after,” the fashion was as vintage as ever.
If you’re anything like me, you’ve been tempted to copy Summer’s entire quirky, blue-hued wardrobe—from her tea-length dresses and cutesy hair bows to her ruffled blouses and billowy skirts. But we’re looking at fall outfits here, which is why day 265 stands out the most. On this day, she and Tom are at the park, and she’s wearing a sweater vest paired with a white button-up, a loose-fitted neck tie, and a mini skirt. Adorable.
sweater vest / button-up / skirt / tights / tote bag (under $30) / loafers
5. To All The Boys I’ve Loved Before
Lara Jean’s antics make me feel all sorts of nostalgic for my own teenage years. But one thing is certain: My high school wardrobe could have never competed.
If it was possible, I’d copy and paste Lara’s whole closet into my own. (Seriously, does anyone know where her stylist shopped?). One outfit in particular that I want to copy doesn’t actually seem like a fall outfit. Florals for fall? Actually groundbreaking. Lara is breaking the rules, and you can too.
bomber jacket / dress / backpack / sneakers
6. When Harry Met Sally
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 / necklace / skirt / tights / loafers
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