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

Haven’t you heard? It’s Meg Ryan Fall.

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.

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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.

Nothing says fall more than a plaid print.

Sally made florals fall-friendly with a micro-print version.

A chocolate-brown trouser is so fitting for fall.

A more modern-day take on Sally Albright’s shoulder bag.

These cozy cashmere-wool blend gloves will keep you warm all fall long.

Are bowler hats due for a comeback?

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.

Annie’s look is a sweater set, but if you want to keep it simple, this crewneck comes in a similar blue shade.

Layer this short skirt with tights when the temps drop.


A slightly more stylish version of Annie Reed’s necklace that you can dress up or down.

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.

A fall wardrobe isn’t complete without a cozy cardigan.

Khakis fan or not, this wide-leg pair from Dickies will go with anything.

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