Fall is well underway and October is here, meaning the holy trinity of months is upon us and it’s time to break out the fisherman sweaters, start perfecting your hot chocolate recipe and sit down for the annual viewing of the Meg Ryan Trilogy. You know, only the most wonderfully classic fall-into-winter rom-coms ever made. With When Harry Met Sally leading the charge, followed by Sleepless in Seattle and You’ve Got Mail, the idea of a “Meg Ryan fall” has been all over the internet recently, and for good reason! It’s hard to say exactly where this trend began, though I’ve been following its growing popularity on Twitter as people post their own takes on the outfits and general aesthetics from The Trilogy, but I can say with complete and utter certainty that there are no better movies to watch than these three at the start of the season. These movies perfectly encapsulate the romanticism of the end-of-the-year months through fashion, sound, and story, and I’m here to guide you through each one.
When Harry Met Sally transports us to New York City in a sea of gold leaves where everything is accompanied by Harry Connick Jr’s lovely voice and everyone’s clothes are a perpetual palette of reds, golds, and browns. The movie follows Harry and Sally, two friends who keep running into each other over the course of several years, trying to decide if they can really ever be just friends. There’s a lot of scenes featuring loungewear (knitted socks, robes, and a very cozy-looking pair of pajamas) which immediately invoke feelings of nights spent curled up reading or on the phone with your friend who you wish was more than your friend…if you’re Harry and Sally, that is. This movie in particular appears to be the face of the internet’s obsession with Meg Ryan, and it’s clear why. Is the denim awful in this movie? Absolutely. But who cares about that when Sally is wearing the world’s most beautiful (and extensive) array of sweaters and blazers, paired to perfection! It’s iconic, but the real showstopper is the white fisherman sweater that Harry wears in his apartment. You know the one. It is glorious, perfectly ties together this film’s warm and cozy vibes, and we are in the perfect place to acquire one, so watch this movie, romanticize your walk as the leaves begin to turn, and spend your whole paycheck on a fisherman sweater. Just blame Harry!
You’ve Got Mail is perhaps my favorite of the trio, likely because the cozy, Christmas-decorated bookstore that Meg Ryan’s character runs is featured essentially as a main character. A new, modern bookseller store comes in to try and replace the local, beloved bookstore, as characters Kathleen and Joe fall in love over email, completely unaware that back in the real world their stores are locked in competition. It’s funny, sweet, and the idea of this tiny local bookstore nestled in the Upper West Side is the stuff dreams are made of. In terms of design, this movie exhibits peak seasonal fashion. Meg Ryan brings the classic dress and tights combo back into play, traipsing around the city while The Cranberries play in the background, or sitting with a coffee accompanied by some jazzy Louis Armstrong. The Christmas spirit has never been stronger. And that grey turtleneck she wears in the bookstore against a background of string lights and rows of bookshelves? To die for. After watching this I promise you’ll want your new career path to include running a small bookshop, writing children’s books, and wearing only turtleneck sweaters.
Sleepless in Seattle is like a love letter to layering. Sweaters, blazers, coats, scarves—they all play necessary roles in rainy, chilly Seattle. In a nutshell, Sleepless in Seattle is about recently widowed Sam and his son Jonah who are flooded with fanmail after Jonah calls into a radio show and gets Sam to talk about how much he misses his wife. Annie hears their story and somehow falls in love from 3,000 miles away, and the movie is essentially her trying to make her way to this man who she has never met yet is convinced is her soulmate. I don’t think this is Meg Ryan’s most fashionable character, however I would argue Jonah steals the show here. His airport outfit, an oversized sports crewneck paired with shorts and a baseball cap, is an ensemble I see recreated on social media daily. This kid is like eight and he’s providing airport style inspo for Instagram influencers everywhere. He also boasts a wide array of knitwear, sweatshirts, and jackets which are clearly influenced by his father, because Tom Hanks wears a lot of bomber jackets in this movie, and I mean a lot. He’s got one for every occasion, though his most notable might be the beige, suede-like piece that he wears during the final scene on top of the Empire State Building. It’s impossible to watch Sleepless in Seattle and not feel warm and fuzzy, with the soft soundtrack of Nat King Cole and Gene Autry and the scenes of people falling in love in the city. It’s dreamy, and there’s no other way to describe it!
While some elements of the storylines in these films are admittedly problematic, their aesthetic and style are solidified in cinematic history, and will forever provide audiences with the perfect cold-weather viewing. Seasonal rom-coms are the best way to wind down and kick back after you’ve submitted that first essay, want a good night in with friends, or just feel like being inspired to romanticize your life a little more, and the 90’s manage to get it right every single time. Norah Ephron has absolutely outdone herself with these movies, and has somehow inspired the entire internet to start dressing like Meg Ryan and listening to Harry Connick Jr at all times, and I don’t think anyone’s mad about it. No matter your reason, it’s not fall until you’ve watched The Trilogy, so get to it!