Meg Ryan Fall Style: 8 Rom-Com Inspired Outfits
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Meg Ryan fall is officially here, and I couldn't be more excited. Imagine New York in autumn: charming storefronts, cozy apartments, and that crisp fall air that makes everything feel just a little more magical.
What makes Meg Ryan’s ‘90s flicks even better for fall? Her style. From cozy sweaters to timeless trench coats, Meg Ryan’s fall wardrobe is the definition of cozy yet polished—perfect for the autumn season.
In this post, we’re taking a closer look at how to get Meg Ryan’s fall style by breaking down eight outfits inspired by some of her most beloved rom-com roles.
Whether you’re looking to recreate her look from When Harry Met Sally or channel her more minimalist vibe from You’ve Got Mail, these outfits will help you channel the autumnal aesthetic that defines Meg Ryan's movie style.
When it comes to fall fashion, we’ll definitely have what she’s having!
When Harry Met Sally
Some of the most memorable Meg Ryan style moments come from When Harry Met Sally. In the film, her character, Sally Albright, sports a variety of autumn-ready outfits, including classic pieces like cozy sweaters, tailored coats, high-waisted jeans, and ankle boots. While a few pieces (like her iconic bowler hat) certainly reflect the era, most of her outfits still feel remarkably timeless, even 35 years later.
1. Suede Jacket + Red Sweater
If there’s one outfit that screams classic fall, it’s the suede jacket and red sweater combo from When Harry Met Sally. And with both suede and red trending in fall 2024, this look could not be more on-trend.
The suede jacket is a piece that instantly elevates any outfit. It has that rugged, yet refined vibe that pairs perfectly with fall's earthy tones. Throw it over a red sweater, and you’ve got yourself a striking color combination for fall.
Pair it with fall classics like dark-wash denim, ankle boots and a matching tote bag, and you’ve got the kind of outfit you can wear just about anywhere—whether you’re running errands, meeting friends, or walking under the autumn leaves.
2. Cable Knit Sweater + Leather Skirt
Another look featuring the color of the season is this red cable knit sweater and leather mini skirt combo. The cable knit sweater is a fall staple—it’s cozy, it’s warm, and it has that classic, homey feel that makes you want to curl up by the fire. But paired with a leather mini skirt, it takes on a whole new life.
This outfit is the perfect example of how to mix textures for fall—the sweater adds softness, while the leather mini skirt brings in a bit of edginess.
You can dress it up with a pair of heeled boots or keep it casual with some loafers or ballet flats. Either way, it’s a look that was made for fall.
3. Mockneck Sweater + Jeans
Meg Ryan’s character Sally Albright in When Harry Met Sally knows how to do casual fall style, and this outfit is a perfect example. A mockneck sweater, high-waisted jeans, and ankle boots create a timeless combo that’s simple, comfortable, and effortlessly chic.
The mockneck sweater offers just the right amount of warmth without the bulk, making it a sleek alternative to the turtleneck. Pair it with dark-wash, relaxed-fit jeans, and you’ve got a go-to autumn outfit that’s perfect for all your favorite fall activities.
Ankle boots are the finishing touch that pulls the whole outfit together.
This outfit is the epitome of Meg Ryan fall style: easy, cozy, and effortlessly chic. It’s the kind of look you can throw on without thinking and still look like you stepped out of a 90s rom-com.
You’ve Got Mail
In You’ve Got Mail, Meg Ryan’s character, Kathleen Kelly, is the epitome of ‘90s minimalist fall style. Her wardrobe in the film is filled with sleek silhouettes, chic separates, and classic knitwear—all perfect for layering during the cooler months. The key to nailing her look is to focus on neutral colors like black, beige, and gray, which are staples of the Meg Ryan fall style.
4. Black Basics
Turtleneck / Skirt / Boots / Bag
Running into your nemesis at a party has never looked so stylish. Kathleen Kelly’s monochromatic ensemble is undeniably chic for fall. It starts with a sleek black turtleneck for a sophisticated yet cozy foundation. Paired with a classic black pencil skirt, her look is polished and modern—perfect for transitioning from the office to an evening out.
It’s unclear the exact shoes she’s wearing (though I can imagine her signature loafers), so I’ve styled the outfit with knee-high black leather boots for a sleek update. A structured handbag with a gold clasp ties the look together. This all-black ensemble is a perfect example of how sometimes, simplicity is truly elegant.
5. Wool Coat + Loafers
This outfit is preppy, polished and effortlessly charming—just like Meg Ryan’s character Kathleen Kelly in You’ve Got Mail. The centerpiece is a classic charcoal black wool coat, a versatile staple that adds both warmth and structure to any fall ensemble. It's perfectly paired with a knee-length plaid pencil skirt in timeless brown tones.
To keep the look cohesive and practical for cooler weather, black opaque tights seamlessly transition into glossy black loafers, which add that perfect touch of prep. The minimalist black leather shoulder bag ties everything together in this effortlessly chic fall look that’s ideal for a cozy day in the city, a casual coffee date, or strolling around town, pumpkin in hand.
6. Knit Separates
Meg Ryan fall calls for cozy knitwear, and this look is no exception. She layers neutral tones to create an ensemble that feels both comfortable and refined. At the core of the look is a soft camel-colored sleeveless sweater, which serves as a warm base layer, and a matching camel cardigan layered over top.
Another staple of Ryan’s rom-com style, a classic black pencil skirt, creates a polished silhouette. Classic loafers (or Mary Janes, as I opted for) and a sleek black tote bag pull this look together.
Whether you're heading to a cozy date night or a casual day at the office, this outfit is a perfect example of how to stay comfy, yet stylish this season.
7. Shift Dress + Turtleneck
Dress / Turtleneck / Tights / Boots
One of my favorite looks from You’ve Got Mail is this simply chic combination. A brown shift dress layered over a black turtleneck brings together comfort and elegance effortlessly.
Meg Ryan fall style is all about mastering the art of thoughtful layering. Autumn brings constant transitions—between temperatures, seasons, and activities—so your wardrobe needs to keep up. Meg’s movie looks are often a mix of textures and layers, combining the soft with the structured, the light with the heavy. This look is the perfect example!
Finish off the look with a pair of knee-high boots or classic loafers or ankle, and you’ve got an outfit that’s as cozy as it is chic. From Thanksgiving dinners to coffee dates, this outfit is perfect for a variety of fall occasions.
Sleepless in Seattle
Sure, Sleepless in Seattle begins during Christmas, not fall. But don’t overlook Annie’s outfits—there are some gems of autumn inspiration in there too. I’m particularly inspired by her loungewear looks that are so easy to copy this fall.
8. Gray Loungewear
Sweatshirt / Joggers / Socks
For those cozy fall days at home, take a cue from this gray loungewear look. This outfit is the definition of comfort, and it’s proof that you can look stylish even when you’re just lounging around the house. Sometimes, a soft loungewear set is all you need. Add some thick crew socks, make a cup of tea, and you’re ready to enjoy a quiet fall afternoon at home (maybe watching your favorite Meg Ryan film).
Meg Ryan Fall Wardrobe
Meg Ryan’s fall outfits are iconic for a reason—they’re easy to wear, they’re timeless, and they perfectly capture the essence of the season. But the best part is that they’re also incredibly versatile. You don’t need to copy her looks exactly to capture the same look. Mix and match the pieces to create your own version of Meg Ryan fall style. Here are some essential pieces to curate your own Meg Ryan-inspired fall capsule wardrobe:
Meg Ryan’s rom-com characters have given us not just unforgettable movie moments but also timeless fashion inspiration that’s perfect for the fall season. By incorporating these eight outfits into your wardrobe, you can easily channel the effortless elegance and cozy comfort that define Meg Ryan’s iconic fall fashion. I hope you’ve found some inspiration from these Meg Ryan-inspired looks!
Which Meg Ryan fall look is your favorite? Let me know in the comments below.
