How Buttoned Styles Meg Ryan's Timeless Fall Looks

Meg Ryan was a catalyst and pioneer of the 90s’ catalog of romantic comedies. Some of her most beloved roles in films such as You’ve Got Mail, Sleepless in Seattle, and When Harry Met Sally are set against backdrops of a New York City autumn led many to instantly associate her with fall time, comfort movies, and simple yet timeless fashion.

While your autumnal experiences may differ from Meg’s roles of meeting strangers on park benches or exploring museums with cups of coffee in hand, her classic, stylish outfits are easy to recreate. Here is how her characters are inspiring us this season!

Using the silhouette of Meg Ryan’s character Sally Albright in When Harry Met Sally, Marlee Melbert styles a chunky, white blouse with a blazer jacket over her shoulder. Her straight, neutral pants taper at the ankle to add structure to the outfit and emphasize her white sneakers. Marlee adds chunky gold jewelry, a red lipstick, and a tote from the Metropolitan Museum of Art to highlight and tie together the fall elements of her look (and it just so happens that some scenes from When Harry Met Sally were actually filmed at the MET Museum!).

Marybeth Daniel channels Kathleen Kelly’s love of layering in the quintessential fall movie You’ve Got Mail. Taking a page out of Kathleen’s style, we consider this look “bookstore-owner cozy.” She layers a long sleeve sweater underneath a simple overall dress, and finishes the look with a dark red lip and brown ankle boots.

Maddie McNamee pulls together a flattering yet simple autumnal look. Inspired by Meg’s Sally Albright, she opts for a slouchy white sweater tucked into straight-legged, high-waisted jeans and a wide brim hat. Maddie’s black Doc Martin boots perfectly balance out her outfit, making this the ideal outfit to roam the streets of New York City in.

Taking inspiration from the patterns in Meg’s diner scene outfit, Ruthann Daniel swaps out the cardigan for an oversized shirt jacket that matches the pants in a monochromatic scheme. She pairs it with a neutral shirt underneath and white rain boots, which keep the outfit simple yet timeless for a Texas fall.

Written by: Ruthann Daniel

Edited by: Greta Gessert

Photos by: Caitlin Rose & Repeller