Every Outfit Sally Wears in When Harry Met Sally

30 years ago, When Harry Met Sally hit theaters. To say that this movie “holds up” would be a massive understatement. It has reached cult classic status, and in the world of romantic comedies, most consider it to be the gold standard (Google “best romantic comedies,” and every list will include When Harry Met Sally, almost always as #1).

What holds up about this movie 30 years later? The cozy fall setting, the writing, the chemistry, the performances, etc. But what about the fashion? This movie is a Master Class in fall layering. Some of these outfits contain so many layers, I wonder if there is even an end to them. Do Harry and Sally even have bodies under these clothes? Or is there just layer, after layer, after layer into eternity? There’s no way to know. To celebrate 30 years, let’s take a look at every outfit Sally wears and rank them on a scale of 1 (heinous) to 10 (glorious).

(Click here for every outfit Harry wears)

Part of me hates this. But a smarter, cooler part of me loves it. I always love an imbalance of weather wear – shorts with a sweater, warm pants and boots with a tank top. I think it’s important to throw people off balance and confuse them with your fashion choices.

8/10 (for low-key adorableness)

The floppy little maroon tie is ridiculous, but it’s also adorable. And Sally’s hair looks incredible in this scene. This may be a little over the top for a burgeoning writer’s airplane outfit, but it is memorable and iconic.

7/10 (for drama)

This jacket has the same sort of plaid as the airplane outfit, but the shape takes it to another (lower, more horrible) level. Hideous plaid jacket with shoulder pads – you are not welcome in 2019! Get thee back to the ’80s from whence you came! A hex upon you!

0/10 (for being unpleasant to look at)

This look is the epitome of fall coziness. It may just be the perfect fall outfit.

9/10 (for warmth)

At first glance, there seems to be just the white shirt under this blue sweater with enormous buttons. But then, at the salad bar, a red sleeve peeps out. Is this a different day? Or are there just unending surprise layers under the enormously-buttoned sweater? Are the buttons functional or decorative?

5/10 (for button/layering confusion)

I mean, I’m not sure what else you would wear to tap-dancing class.

8/10 (for appropriate theme)

I like that Sally feels the need to channel Diane Keaton for a trip to the mailbox. This look may be a tad dramatic for errand-running, and we never get to see the front of it, but I love the cut of that blazer.

7/10 (for Diane Keaton vibes)

This is probably the most memorable and iconic outfit from the movie, and I can see why. It takes a certain bravery to mix so many neutrals in one outfit. Black, brown, gray, taupe – we have it all. This look is cemented in 1989, and I don’t see anyone being able to pull it off in 2019, but it gets high points for being memorable and fun.

8/10 (for being iconic)

A few moments before this scene, Harry tells Sally, “you should wear skirts more, you look really good in skirts.” I have always loved that line, and thought it was really sweet that the only time you see her in a skirt is directly following that interaction. Until I got into this fashion deep dive and discovered that… this is not a skirt! It is shorts!! Sally’s not changing her out of pants for anyone, not even the love of her life.

10/10 (for the hidden feminist message)

Sally’s hair is a fluffy, charming, ’80s mess and she looks so cozy. But I think this outfit would have aged a lot better without the strange buttons and medallion on the white shirt.

6/10 (for the medallion)

The real star of this outfit is the hair; the little fountain pony is adorable. But the dress is great too! You cannot beat this as a late ’80s party lewk.

10/10 (for being an unbeatable party vibe)

I am here for this Elinor Dashwood-approved regency-era vibe.

9/10 (for the nerdy historic feel)

These jeans are an affront to butts throughout all of time and space. What did butts even do to you, ’80s?

2/10 (for the butt)

This dress is outside of Sally’s usual style, but Meg Ryan looks so sweet and pretty in this dress, I can’t help but love it. A+ on the hair.

8/10 (for sweetness)

It’s a bathrobe. But it does get her laid.

10/10 (for practicality/plot importance)

This is less of a lewk and more of a major mood. Casually lounging on a loveseat, eating snacks with the carelessness of someone who doesn’t actually need food to live, all while not even trying that hard to pretend like you care that your best friend is trying on wedding dresses. Plus, this is basically a more grown-up version of the outfit we first see her in.

10/10 (for the mood)

Although I love the emerald green on her, I do not love the evil stepsister vibes.

4/10 (for the fact that it is a bridesmaid dress combined with the Drusilla vibes)

I think we can bring this hat back for fall 2019. Who’s with me?

8/10 (for the hat)

This is the perfect working-from-home look for any decade, periodt. The turtleneck looks comfortable, but still classy. Those glasses went out of style for a couple of decades, but they are majorly back in. And her hair? Her hair is INCREDIBLE. I can only dream of my hair ever looking this amazing. BRB, going purple turtleneck shopping.

10/10 (for being perfect)

I told thee to get!!

1/10 (for continuing to be hideous, and somehow returning)

The worst thing about this outfit is the fact that we barely get to see it. The best thing about it is definitely the arm warmers.

10/10 (for the arm warmers)

This is the worst her hair looks the entire movie, but the shirt is ok.

5/10 (for the bad hair)

I’m not sure what your plans are this weekend, but you need to make sure they include a re-watch of When Harry Met Sally. Or, if you have never seen it (shame on you!), a first watch. I promise it will be worth a couple hours of your time.

Don’t forget to check out Harry’s outfits!


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8 comments

    • I just have to know if you were in your 20s when When Harry Met Sally came out. I’m guessing you were younger? Were you alive? And please understand, that I love and agree with your comments for the most part. Sally’s style was an inspiration to me in 1989 and for several years afterward. The blazers, the blouses, the hair! So much to love. Anyway, I know it’s been a minute since you wrote this piece, but I just found it. So, thanks for your input on one of my favorite movies with some of the best characters ever written. You made me laugh and miss those turtlenecks and high waisted jeans.

      Like

  1. I love this post and your affection for Meg Ryan’s sartorial style in When Harry Met Sally…
    I’m not fashionista but even after 30 years Sally’s hair rocks in every single scene.

    Liked by 1 person

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