Every Outfit Harry 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 Sally wears)

Jeans, nondescript zip-up hoodie, baseball tee – this is every lazy, slightly obnoxious guy I had a crush on in college. I can’t decide if I want to kiss or punch Harry, which I believe is the point.

8/10 (for college-crush-cuteness)

Harry has left his childish days of non-descript hoodies and baseball tees behind in favor of this look that makes me feel like he is trying a little too hard to look like a real grown-up. And one of the most important things one realizes when one becomes a real adult, is the importance of keeping one’s core warm. Sweater vests are a must for your real adult closet. Trying-to-hardness aside, this is a good look on Harry, and I am always on board with rolled up sleeves.

7/10 (for the rolled up sleeves)

I feel like I should hate this sad, recent divorcee vibe of denim on denim, but I don’t. The double denim + camel blazer belies a Harry who is not trying quite as hard, and it shows. In a good way.

9/10 (for the welcome effort reduction)

The moss green and maroon color combination is something I hope to never see again. Unacceptable.

1/10 (for the distressing color combination)

And, so, sad divorcee gives way to depressed, lonely bachelor. So depressed he can’t even purchase furniture for his apartment. But this is a great weekend lewk, and I am very grateful that open, plaid button-downs are coming back in.

7/10 (for being adorably pitiful)

This is the greatest sick day outfit anyone has every worn. Chunky sweater, sweatpants, and the thickest looking socks I have ever seen. I want to be either wearing this myself, or cuddling Harry while he wears it. I don’t even mind if I catch his cold.

10/10 (for extreme coziness)

The layers around the neck area feel like a fun-house mirror. I can’t tell where the layers end and Harry begins. And the white sneakers with this are just not working. It feels like he put so much time into adding a ridiculous amount of layers at the top, then ran out of energy when he got to the bottom half.

4/10 (for looking too itchy)

Wearing a mock turtleneck to bed belies a level of commitment to the mock-neck life that I can only aspire to. Harry has lounge wear down.

10/10 (for commitment)

Harry is at his best in casual wear, and his worst when he is trying too hard. The pattern on this sweater is a travesty. I’m glad he left the sneakers at home for this, but the sweater and poorly fitting jacket just make me feel sad.

3/10 (for making me feel sad)

I’m really torn about this one. If you’ll remember – this is Harry’s sick day sweater. I have a pretty strong personal policy against wearing my sick-day clothes in public. But he is technically in his own home for this scene, so maybe I will let it slide.

6/10 (because, sick or not, it’s a great sweater)

Every time I look at this photo, I have a sense memory of what it feels like to wear a t-shirt over another t-shirt, and I do not like it. Find another way to stay warm, Harry! Or are you trying to stay cool? I don’t know. It makes me sad to think about how much time he must have spent rolling up sleeve after sleeve, only to look this dumb.

2/10 (for the unpleasant sense memory)

This dad vibes are wafting off of this sweater like the scent of cheap cologne. But I appreciate the fact that he is wearing the denim button-down underneath. Glad to know he hasn’t abandoned his entire sad divorcee closet.

5/10 (for the dad vibes)

The shoulder pads in this suit are not good, and it does not fit well. But I love the black grid pattern t-shirt with the black tie.

6/10 (for the black on black)

I just… don’t do this. Why? Everything about it is confusing. That blazer looks uncomfortably heavy, and I can’t begin to imagine why he felt the need to button every single button on that polo. No wonder Princess Lea didn’t want to date you.

2/10 (for the excessive buttoning)

This outfit loses all 10 points for being boring and awful, but gains every single one of them back due to the fact that Billy Crystal is easily at his most adorable/attractive in this scene. He’s so fun and flirty, then vulnerable and sweet.

10/10 (for the peak Harry hotness)

Dressing like an industrial era itinerant artist, a la Jack Dawson, might be an acceptable choice for some settings. A casual game night with friends it not one of those settings. I am all for a wildly dramatic outfit, but a night in with friends is neither the time, nor place.

4/10 (for the setting)

Jeans and a black sweater is a perfect look for any human being, and I love the secret layered stripey tee that we only get a glimpse of as he throws his clothes on in the morning to ghost the love of his life.

9/10 (for being classic)

BORING. AND YOU CANT EVEN SEE IT. I hate this look so much. But I guess if you are trying to make sure your best friend doesn’t want to sleep with you, this look could do the trick.

1/10 (BECAUSE)

NO. NO! What can I even say? No! This is heinous. It hasn’t aged well at all. This was only a cool thing to wear exactly in 1989, and I’m not sure it was even cool then.

0/10 (you can see why)

This is by far one of Harry’s worst looks. This tie haunts my nightmares, and the makeup team went a little overboard with the blush. It doesn’t help that Harry is a huge asshole in this scene and easily at his least adorable/attractive.

2/10 (for containing a jerk)

No thanks.

1/10 (for being boring and ill-fitting)

Ok, again, Billy Crystal is very sexy here. This look is a combination of all of the elements that have made previous outfits adorable – casual weekend vibes, rolled sleeves, karaoke machines, and some self-deprecating humor.

10/10 (for culminating all of Harry’s cute factors)

He’s wearing the sex night shirt. I, for one, think this is a thing. Also, is that a carton of milk in the background?

8/10 (for the sex night shirt)

Harry finishes out the movie with some characteristic layers and dad-vibes.

6/10 (again, for the dad vibes)

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 Sally’s outfits!


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