At long last, Meg Ryan fall is finally here again. For the uninitiated, allow me to explain: Ryan’s many characters in ’80s and ’90s rom-coms (think: When Harry Met Sally and You’ve Got Mail) had lush, autumnal wardrobes like none other. From the chunky knits and oversized blazers to the various textures, layers, and neutral tones, her characters were the masters of cozy style.

Now that the weather has finally dropped below 50 degrees here in NYC, it couldn’t be a better time to look back at her most iconic looks for outfit inspiration. Here, 7 ways I am channeling Ryan this fall.

The Cozy Look

meg ryan youve got mail

Does it get any more cozier than this? Ryan’s character in You’ve Got Mail struck the perfect masculine/feminine balance with a black wool coat, tweed skirt, chunky brogues, and a bright neck scarf for a pop of color. It’s very ’90s. Just don’t forget accessorize with a pumpkin from your local farmers’ market.

Plaid Wool Blend Reefer Coat

Lauren Ralph Lauren Plaid Wool Blend Reefer Coat

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Cara Houndstooth Pencil Skirt

A.L.C. Cara Houndstooth Pencil Skirt

Matte Opaque Tights

WOLFORD Matte Opaque Tights

Lyla Lug Sole Derby

Coach Lyla Lug Sole Derby
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Laurel Canyon Silk Bandana.

Laurel Canyon Silk Bandana.

The Chunky Sweater Look

meg ryan chunky sweater in when harry met sally

Everett

If there’s two things to take away from Sally Albright in When Harry Met Sally, it’s that 1) a chunky, cable-knit sweater is a fall n0-brainer and 2) a bold color will always add pizzazz and liven up an ordinary outfit.

Aran-Knit Wool-Alpaca Turtleneck

Polo Ralph Lauren Aran-Knit Wool-Alpaca Turtleneck
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Vesey Pencil Skirt

Marcella Vesey Pencil Skirt
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Lattice Net Tights

Commando Lattice Net Tights
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The Day Glove

Everlane The Day Glove

Now 25% Off

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Texture, Neutrals, and Layering

meg ryan in when harry met sally

Everett

Another Sally Albright classic. Ryan’s character played with textures, neutral tones, and layering, and somehow made it all mesh perfectly together here. And besides, is it really an autumnal look if you’re not incorporating one or all of these style aspects?

Ross Packable Wool Fedora

Janessa Leone Ross Packable Wool Fedora
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The Oversized Blazer in Wool

Everlane The Oversized Blazer in Wool

Now 25% Off

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Heart-Embroidered Intarsia-Knit Jumper

Moschino Heart-Embroidered Intarsia-Knit Jumper

The Harlow Superwide-Leg Trouser

Madewell The Harlow Superwide-Leg Trouser

The Andie Loafer

Margaux The Andie Loafer
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Vegan Leather Slouchy Tote

Banana Republic Factory Vegan Leather Slouchy Tote

Now 40% Off

Cashmere Lined Leather Touchscreen Gloves

Nordstrom Cashmere Lined Leather Touchscreen Gloves

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Crew Hoops

Gorjana Crew Hoops
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The Lush Suede Look

meg ryan suede dress you've got mail

Everett

With suede having a major moment this season, I am most excited to channel this You’ve Got Mail outfit. I love the way she styled a suede shift dress over a black turtleneck sweater—another prime example of playing with texture and layers. It’s also proof that brown and black do pair well together.

Chocolate Faux Suede Billie Mini Dress

Hyacinth House Chocolate Faux Suede Billie Mini Dress
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'Luxe' Leg Shaping Tights

SPANX ‘Luxe’ Leg Shaping Tights

Stretch Boot in Espresso Nappa

Emme Parsons Stretch Boot in Espresso Nappa

The Brunch Look Aesthetic

meg ryan youve got mail

Everett

A camel cardigan paired with a simple white t-shirt will never disappoint. In You’ve Got Mail, Ryan styled hers with a gray skirt, which added a surprising touch to the pared-back look. But if that’s too much to tango with, a pair of mom jeans, or even, barrel legs jeans would make your look *chef’s kiss*.

Classic Crew Wool Cardigan

Almina Concept Classic Crew Wool Cardigan

Lexy Tee

Michael Stars Lexy Tee

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Double-Faced Wool Midi Skirt

Cos Double-Faced Wool Midi Skirt

The '90s Creased High Waist Straight Leg Jeans

Madewell The ’90s Creased High Waist Straight Leg Jeans
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The Statement-Maker

meg ryan proof of life

Everett

Sure, Proof of Life isn’t exactly what you’d call a classic Meg Ryan rom-com, but you can’t deny how perfectly autumnal this outfit is. She’s quite literally wearing two of the hottest colors of 2024 in one look: burgundy and chartreuse. Here’s your chance to take brat girl summer into fall.

Linde Faux Leather Jacket

Ronny Kobo Linde Faux Leather Jacket

Kavya Striped Rib-Knit Blouse

Veronica Beard Kavya Striped Rib-Knit Blouse

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Bias-Cut Silk Midi Skirt

La Ligne Bias-Cut Silk Midi Skirt

Tall Banana Boot

Tory Burch Tall Banana Boot

The Essential Camel Coat

meg ryan in hanging up

Everett

I’ve said it before, and I’ll say it again: a camel coat is the little black dress of outerwear. You can dress it up or dress it down (as Ryan did here in Hanging Up), and it still looks fantastic. Here, are some similar options to shop.

Classic Wool-Blend Straight Coat

Vince Classic Wool-Blend Straight Coat

Manuela Icon Coat

Max Mara Manuela Icon Coat
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Single Breasted Wool Blend Reefer Coat

Sam Edelman Single Breasted Wool Blend Reefer Coat

Now 36% Off

Headshot of Sophie Dweck

Sophie Dweck is the associate shopping editor for Town & Country, where she covers beauty, fashion, home and décor, and more. 

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