It’s been 30 years since Nora Ephron sparked the debate heard round the world: Can men and women be friends? It's the question at the heart of When Harry Met Sally, a movie famous for romance, incredible dialogue, and Meg Ryan faking an orgasm in a Jewish deli.
But to celebrate the movie only for that is to overlook something vastly more iconic: Harry Burns’s looks. Someone, somewhere made Billy Crystal a handsome rom-com lead instead of the funny-looking voice of Mike Wazowski. It wasn’t just the script that made Harry bangable, that made us root for Sally Albright to date this miserable cynic; it was his fashion, and no one can convince me otherwise.
That they took a man with a face for Oscar hosting and turned him into a certified hottie who has his proverbial shit all the way together is a feat worth celebrating. So, in honor of the 30th anniversary of When Harry Met Sally, a.k.a. the Best Film of All Time, I’ve ranked every single outfit that Harry is seen in onscreen. My qualifications include: have watched When Harry Met Sally at least 29 times.
32. This look is awful and I refuse to defend it. The beard looks great, so I’ll let him have exactly one point for that. Otherwise, he looks like Santa’s evil corporate toy-store-owning twin brother in a Lifetime Christmas movie. You have to be thoughtful with maroon. You can’t just put a weird grayish green next to it and hope it works. You look like if Barney the Dinosaur became a tax accountant. Later in this movie, Sally ugly-cries to Harry saying, “I’m difficult!” and that, right there, is the exact energy of maroon.
31. Here is a photo of Harry wearing this dumb-ugly coat to purchase a Christmas tree. Let’s move on!
30. A gray T-shirt? To bed? Groundbreaking.
29. Passable for a job interview, but Harry can do better and we all know it.
28. Here is Harry’s uninspired post-sex dinner outfit. I suppose when you hook up with your closest female friend and you’re trying to communicate that you don’t want this to become a thing, you don’t want to get too jazzy. And it is nice that his I-hope-we’re-okay-after-hooking-up dinner includes both a cloth tablecloth and a blazer.
27. Akfja;slkdjfasdf WHAT? Why did he roll up the sleeves of his short-sleeve sweatshirt that he inexplicably paired with a long-sleeve shirt underneath? Are you hot or cold? What are these terrible school-issued gym-class pants? Throw this whole outfit into the SUN.
26. Yet another characterless low-point look; nothing to see here.
25. Another look inspired by the sad fact that he and Sally are on bad terms. He’s binge eating Mallomars and leaving her sad voicemails, and I can’t be the only one who thinks it might be A Thing that he’s wearing the shirt he wore over to her house when they hooked up because it reminds him of her!
24. It’s a bit difficult to see this outfit, but just trust me that depressed Harry—who is in the middle of trying to make an apology phone call to Sally—looks pretty humdrum here. It’s nothing to base an outfit off of. One thing of note: He’s got his sleeves rolled up to three-quarter length, which is always provocative; I can’t encourage you enough to do so at every opportunity.
23. Here comes our big corporate sweetie! Things have changed. Harry is a political consultant now, he’s about to be married, and he owns a sweater vest. (And a portfolio! Weren’t the '80s quaint?) This look is the antithesis of horny, which is unfortunate, because it’s Harry and Sally’s real adult meeting. I would advise that most men should never wear a sweater vest around anyone whose naughty bits you actually want to see. The sweater vest says: I cannot commit to either sweaters nor vests, and have instead chosen to dive headfirst into ugly.
22. Who wears a turtleneck to bed? And why am I so into it?
21. This suit is bad. It’s like someone cut the suit in an effort to make Billy Crystal look even shorter. This is what a fat-cat golfer wears to Mar-a-Lago.
20. Harry, my sweet angel, what is this weird two-button polo situation? I hope someone else knows what this type of shirt is called and tweets at me angrily to explain what this weird almost priest’s cossack situation is. The jacket is yet another delightful tweed pattern—and a great fit on Harry—and it’s ruined by this odd black shirt.
19. Here is Harry now that he has finally wed Sally, and he looks great because he’s happy. It’s an unimpressive outfit, but who cares? They’ve finally figured out what we all knew from the very first scene: that they’re supposed to be boning for all of eternity together.
18. A boring outfit for one of the best scenes of the whole movie. Truly, I can only imagine how chagrined Harry was to be wearing this the first time he saw his ex-wife, Helen, post-divorce. (And with her new man, Ira, no less!)
17. I love a baseball cap with a regular, everyday outfit. It’s a bit sloppy, but it was raining in this scene, and I don’t think anyone should be judged for outfits they pull together in the rain.
16. Before you get your knickers in a twist, Harry didn’t get to choose this outfit as best man, so I’m not even sure it’s fair to judge it. Also, almost every other look at Marie and Jesse’s wedding is full-on '80s-tragic, so in comparison Harry is positively murdering the style game. (Google Carrie Fisher’s wedding dress in this movie if you want to cringe.)
15. He looks like a '90s divorced dad who takes his kids to Bob Evans on the weekends because all he has in the fridge is Coors Banquet and Hungry-Man frozen dinners.
14. This is our very first look at Harry Burns, and well, this outfit is…fine. The outfit does a respectable job of introducing us to Harry’s love for light-wash jeans, which are really the third protagonist of this film, after Harry and Sally. It is in this schlubby getup that Harry famously declares that “men and women can’t be friends”...right before he goes and establishes a years-long friendship with Sally.
13. That jacket is like if Karamo Brown and Paul Newman had a fashion baby. But let us address the elephant in the room: that horrendous sweater. It looks like something a guy in a band that’s almost famous dug out of a bin at Goodwill and now wears ironically. The sweater looks like what a printer spits out to test ink levels. It almost undoes any of Harry’s raw sexual power that he brings to the film. If only God would deliver us from that sweater.
12. Black doesn’t read well on screen, so you’re just going to have to trust me that this luxurious sweater is a spicy meatball of a look. Harry understands classics and layering like no other leading man in recent memory. Why do I know what’s underneath? Well (spoiler) horny Harry Burns sleeps with Sally in this scene after coming over to comfort her—SEXY OF HIM—and so we get to see him arrive in a nice fall jacket. Then we see the cable knit sweater, then we get to see Harry naked, and then when he’s sneaking out in the morning, we see the goth-ish striped shirt he has on underneath. The man is a master of layering, if not tactful hookup exits.
11. CAN YOU BELIEVE THIS OUTFIT??!?! The second Billy Crystal pops up onscreen power walking in his little leggings, I scream. It’s amazing. Harry Burns walked so that Instagram influencers could run.
Do I recommend this look for the modern man? I’m not even sure. It’s such a pure, unadulterated delight that my heart says yes. But would a lycra legging on any other body look as sweet? Unknown.
10. Here she is: Harry’s last outfit of the movie. His final look in the narrative arc of the film. To the very end, our boy loves his layers. He paired it with a fabulous olive green bomber jacket, which he wore to wander around New York alone on New Years, eating half an ice cream cone and being depressed about his love life. (Who can relate!)
The look he wears to a New Years Eve party to declare his undying love for his best friend Sally Albright. Hard to know if the inside out sweatshirt is a style choice, or a marker of the urgency he felt to tell Sally how he felt. Either way, I adore it. Sally is forced to say yes just because of his sartorial choices.
9. Please don’t shout at me, but this look does it for me. It’s very much a “rich man spending the summer in a rented villa on the Mediterranean” and that is undeniably horny. It says you have money and might take me to Italy.
8. At first glance, there isn’t much to see in this outfit, other than perhaps a lesson on cold weather accessorizing courtesy of Harry’s pop-of-color red scarf and thick leather gloves. (What happened to men wearing gloves? Global warming? Phones with touch screens? OJ? Bring back gloves!) No, the real reason this outfit gets such a high ranking is that beard.
Is a beard part of your outfit? I don’t know. Am I cheating? Probably. But here’s the thing: This beard transforms Harry into a full on mega-hottie, and I refuse to erase that fact from the history books. Fellas who can rock a beard: let Billy Crystal be your inspiration. Is his the best beard of all time? (Insert James Harden eye roll)—no, God, no. But it’s a testament to what a beard can do for your face, and what this beard did is it took Billy Crystal from a baby faced cynic in need of therapy to a sad-sexy divorcé whom I need to help via sleeping with him.
7. This look involves almost every staple in Harry’s wardrobe thrown together: light-wash fitted jeans, white sneakers, a professorial sports coat, a sweater vest, layers, autumnal color palate, etc. It’s quintessential Harry, a signature look, and I can fully appreciate those days when you just put on all of your favorite things and let Jesus take the wheel.
6. This outfit is the most perfect sick day outfit of all time. He even has all his little sick day accoutrements next to him on a tray! Harry knows how to be sick and no one has ever looked more cozy in the history of the world.
5. I feel like I shouldn’t like this look. It’s certainly a drab color palette. I wish he’d take more of a risk in that department, however, I’m letting my own personal horniness decide and here’s what she says: YES. There’s something great about these casual layers. Loose fit up top, tight jeans on the bottom. It just works. Once again, Harry has tucked his shirt into belted jeans, and with it, given us a hint of intention, which is hot. You should want to look intentional, which is not the same as trying hard. It says you care, which is hot. Let us also not forget the thick-knit gray socks with white tennis shoes. I love them.
(Pro tip: Buy warm knit socks, you guys. And not just so that whoever sleeps over at your freezing ass house this winter can steal them.) (But also that).
4. The lesson to learn from this scene: Don’t underestimate the raw sexuality that comes from a well-fitted crew neck sweatshirt with the sleeves pushed up. Also, don’t underestimate how endearing it is to leave a karaoke voicemail apology. It comes only second to Venmo-ing someone $40 in terms of apology rankings.
3. Red alert: I’m about to toss my hat into the Democratic candidate ring and my whole campaign platform is that men look really hot in coats. This ulster coat is elegant, which Harry knows, because he pulled it out on a first date with Carrie Fisher. The date doesn’t work out in his favor, but Harry still got the chance to STUNT on everyone with his fabulous deep charcoal showstopper and tucked in scarf combo. Take note, people who live in cold climates: a good coat is like lingerie for men.
2. All I have to say for this one is look at that sports coat. Look at it. With a denim shirt underneath? And he tucked the denim shirt into a lighter wash pair of jeans? It shouldn’t work! But it does. Because he brings in a brown belt and tucks in the shirt. And because he understands proportion. Okay, hello Harry Burns, I see you. Thank you for dialing up the sexy post divorce with this depressed French literature professor look.
1. Here it is. The best outfit from the closet of Harry Burns. Please note that this is also the outfit he wore while sick, which, yes, means he’s an outfit repeater, which I could not support more. Sometimes I wear the same outfit three days in a row if I’m not seeing the same people.
He’s got on his signature shoes and pants and he’s made a powerful outfit combo out of all of his (and my) favorite pieces. Italian chefs kiss. There’s something about this outfit that makes me want to walk around a park on a crisp fall day with him. I need to date a man who owns a sweater like that; it’s an emergency.
