Private Icon: Meg Ryan In When Harry Met Sally, Sleepless In Seattle, & You’ve Got Mail

Snap/Shutterstock Fashion Haven’t you heard? It’s Meg Ryan Fall. by Maria Bobila Updated: Feb. 20, 2024 Originally Published: Oct. 7, 2021

Now that summer’s coconut girl aesthetic is over, it’s time to fill our fashion moodboards with a new muse for fall: Meg Ryan , specifically for her cult classic ‘90s films, When Harry Met Sally, Sleepless In Seattle, and You’ve Got Mail. The star’s throwback wardrobe has become TikTok’s latest fashion obsession , as users stock up on and show off sweaters (so many sweaters) and menswear-inspired pieces in a neutral color palette for the cozy fall months. Ahead, we picked some of her best looks from her past movies and recreated them so you can have the best “Meg Ryan Fall” ever. We only include products that have been independently selected by NYLON's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Moviestore/Shutterstock When Harry Met Sally (1989) Who knew Sally Albright was such a pro at fall layering? Prints, texture, gloves, a bowler hat — this look had it all.

Cruella Linen Blend Blazer Nothing says fall more than a plaid print. $300 $595 see on Rag & Bone

Moore Micro-Floral Shirt Veronica Beard Sally made florals fall-friendly with a micro-print version. $278 see on veronica beard

Effortless Pant Wilfred A chocolate-brown trouser is so fitting for fall. $148 see on aritzia

Double Loop Bag Cuyana A more modern-day take on Sally Albright’s shoulder bag. $295 see on cuyana

WARMEN Genuine Leather Warm Cashmere & Wool Blend Winter Gloves Amazon These cozy cashmere-wool blend gloves will keep you warm all fall long. $24 see on amazon

Sonoma Wool Bowler Hat Brixton Are bowler hats due for a comeback? $34.97 $78 see on nordstrom rack

Moviestore/Shutterstock Sleepless In Seattle (1993) As Annie Reed, Ryan is giving us some back-to-office (or still WFH) outfit inspiration for fall. Try wearing a matching knitted top-and-sweater set and a pleated skirt.

Shetland Crew Neck Sweater Blue Fia Clothing Annie’s look is a sweater set, but if you want to keep it simple, this crewneck comes in a similar blue shade. $262 see on Wolf & Badger

Matisse Charcoal Pleated Pocket Skort J.ING Layer this short skirt with tights when the temps drop. $69.99

Curved Bar Necklace Common Alloy A slightly more stylish version of Annie Reed’s necklace that you can dress up or down. $80 see on common alloy

Brian Hamill/Warner Bros/Kobal/Shutterstock You’ve Got Mail (1998) Khakis are back! We love this simple and timeless outfit on Ryan as the struggling bookseller Kathleen Kelly. Plus, you’ll be able to wear this for future fall seasons to come.

Crew-Neck Cardigan Sweater for Women Old Navy A fall wardrobe isn’t complete without a cozy cardigan. $34.99 see on old navy

WOMEN SUPIMA COTTON CREW NECK SHORT-SLEEVE T-SHIRT Uniqlo A classic white tee. $14.90 see on uniqlo

Women's Wide Leg Work Pants, Stonewashed Khaki Dickies Khakis fan or not, this wide-leg pair from Dickies will go with anything. $69.99 see in dickies

Private Icon: Meg Ryan In When Harry Met Sally, Sleepless In Seattle, & You’ve Got Mail

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