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Ranking Meg Ryan’s Best Autumnal Rom-Com Outfits

With bonus hair commentary.

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Carrie Fisher and Meg Ryan in When Harry Met Sally.
Photo: Columbia Pictures

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I’ve been thinking about Meg Ryan a lot this month. It all started when I read her essay in InStyle about what it’s like having a famous haircut. Then I read Beca Grimm’s article here on Racked about admiring her layered outfits in You’ve Got Mail. That prompted me to think about how Meg’s When Harry Met Sally outfits are a million times better (sorry, Beca), and that led me down the rabbit hole of her IMDb page. The conclusion? Meg Ryan has worn a ton of really good outfits in movies over the years. Like, a shocking amount of them.

Because her rom-coms were her best work, here is a completely subjective ranking, from worst to best, of the fall outfits she wore in them, plus modern versions to shop.

Meg Ryan on the Empire State Building roof in Sleepless in Seattle. Photo: TriStar Pictures
A dark floral scarf on a model.
Zara Soft Floral Scarf ($25.90)

9. Sleepless in Seattle (1993)

This may be controversial, but I really hate most of her looks — hair included — in this movie. Everything is shapeless and colorless and slouchy and messy, but not in a good Eileen Fisher kind of way. However, this Empire State Building finale look is not terrible, and the thought of hiding under a moody, dark floral scarf is kind of appealing right now.

Meg Ryan in City of Angels Photo: Warner Bros.
Ivy Park Logo Zip Hoodie
Ivy Park Logo Zip Hoodie ($60)

8. City of Angels (1998)

This movie is unintentionally hilarious, therefore it counts as a rom-com. Meg wears scrubs through a lot of this, so this timeless gray sweatshirt she’s in prior to (SPOILER ALERT) dying on her bike is the best fall option here.

Meg Ryan and Kevin Kline in “French Kiss.” Photo: 20th Century Fox
A model wearing a white tee with blue stripes.
St. James x J. Crew Slouchy T-Shirt ($90)

7. French Kiss (1995)

We had some discussion in Racked Slack about whether this counts as autumnal, because I’m pretty sure this is a beach scene (see: Kevin Kline’s white linen suit), but we finally agreed that French-girl striped shirts are seasonless. The hair here is also peak Hershberger, and everyone wanted it.

Meg Ryan in I.Q. Photo: Paramount Pictures

6. I.Q. (1994)

This is a rare period piece for Meg, in which she plays the niece of Einstein (lol) in the ’50s. A very adorable Tim Robbins is a mechanic who attempts to woo her. This is ’50s cosplay at its finest, and she wears all sorts of wasp-waisted skirt suits and dresses. I want all the Peter Pan collars now, and also to dye my hair platinum.

Meg Ryan in You’ve Got Mail. Photo: Warner Bros.
The Group by Babaton Plutarch Sweater
The Group by Babaton Plutarch Sweater ($135)

5. You’ve Got Mail (1998)

Yes, the layering in this movie is very good, but I actually think the best look is the simplest — a big, gray turtleneck sweater. Her hair here is also the most Meg Ryaniest that it ever was and will ever be.

Meg Ryan in Kate and Leopold Photo: Miramax
H&M Wool Blend Coat
H&M Wool Blend Coat ($129)

4. Kate and Leopold (2001)

Meg plays a very serious businesswoman with no time for love. Then Hugh Jackman, a dumb dandy from the 1800s, somehow time-travels to Manhattan and they fall in love. Plot aside, Meg is spectacularly dressed in this movie, with lots of good tailoring and structured jackets and coats. On the downside, this was clearly the height of the flat-ironed hair era.

Meg Ryan as the animated character Anastasia Photo: 20th Century Fox
Topshop Twill Peacoat
Topshop Twill Peacoat ($125)

3. Anastasia (1997)

Does this count as a rom-com? Probably not, but I am counting it because this army green outfit, right down to those booties, is spectacular. This might be the only time Meg has had truly red hair, too.

Meg Ryan in Addicted to Love Photo: Warner Bros.
Tommy Hilfiger Velvet Blazer
Tommy Hilfiger Velvet Blazer ($139)

2. Addicted to Love (1997)

Did anyone see this movie? I definitely did not. In it, Meg and Matthew Broderick’s respective love interests are having an affair, so the two team up to break them up. (Wacky!) This movie features Meg at her edgiest, which you can tell because she mixes leopard with velvet and has a smoky eye. She even wears a feather boa at one point. But this jacket looks very good to my eye now. (A fashion history note: Gwyneth Paltrow wore the famous Tom Ford/Gucci version the previous year at the MTV Movie Awards.)

Meg Ryan and Billy Crystal in When Harry Met Sally Photo: Columbia Pictures

1. When Harry Met Sally (1989)

You probably knew this was going to be number one, but Meg wears various versions of sweaters paired with blazers with such goddamned perfection that I don’t even care that the absolute worst of 1980s denim is on display all through this film.