I’m back with the next post in my series - How To Dress Like Your Favorite RomCom Characters, where I recreate looks from our favorite movies. My last post was also a Meg Ryan movie, but I couldn’t resist doing When Harry Met Sally next since it’s at the top of my list, too.
When Harry Met Sally came out in the late ‘80s and, while I didn’t watch it then (I was five years old - that would have been inappropriate, ha!), I have rewatched the film several times as an adult. It wasn’t the first romcom ever, but it was definitely one of the first of it’s kind. Written by Nora Ephron, this film is a treasure trove of one-liners (I had to include a few in this post), and Billy Crystal and Meg Ryan have such chemistry on screen - it’s magic!
Usually, I’m only recreating looks for the female lead, but I was also inspired by Harry’s kind of casual, cozy, ‘80s wardrobe as well. I included a few of his looks to copy, too. Of course these are masculine in style, but I think they could be just as easily worn by women.
I have here twelve looks (eight Sally, four Harry if we’re counting) in order of appearance.
This look feels retro and modern at the same time! After rewatching this movie for this post (tough job, I know), I was struck by how much I loved this look. It’s so 70s but in a preppy way. And don’t get me started on her hair - Sally has about seven different hairstyles throughout the film from this feathered look to coiled curls to teased and wavy. To say I’m a little jealous is an understatement. Send her stylist over immediately!
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This is one of my favorite looks from the film. I couldn’t tell the exact material of this blazer - it could be corduroy or suede - it’s definitely got texture! She’s wearing it with a red sweater underneath (I’ve linked several options below in case you’re shopping), some dark wash tapered jeans (I went with a straight leg to update the look for modern times) and loafers. The overall look is very sleek and structured with cozy fall vibes.
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And here’s Harry’s look from that same scene - denim shirt, tweed blazer, jeans, and what I think are loafers. Also note the belt - they wear a ton of belts in this film. So ‘80s! I think I have everything in my closet to recreate this outfit.
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Superfans might get mad that I swapped Harry’s Nike’s for these New Balance sneakers, but I have my reasons (namely that I own and can vouch for these).
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Here’s the first appearance of Harry’s iconic cable knit sweater, what is arguably the most famous sweater in all the world. Apparently, the exact source of his sweater is unknown, and Billy Crystal has said in an interview he may have accidentally donated it to the UCLA theater department! Can you even imagine?! I linked a couple similar cable knit sweaters below from Gap and Aritzia - affordable brands we know and love, but if you’re looking for more of a traditional fisherman style like Harry’s, try this Men’s style from L.L. Bean. I’m thinking this would have that big, cozy fit.
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Here’s Sally double checking every one of her pieces of mail before placing them individually into the mail slot (while Harry patiently waits to the side). I love that they made her character unapologetically anal. don’t you? She’s wearing a very businesslike blazer/pant combo here that really balances her big, wild hair. Also, I think it’s time to bring back the glasses chain.
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This is quite the look! I’m not sure I’ve ever seen a bowler hat in real life, but I live in the Midwest so perhaps you have? I don’t think I’d copy this one exactly, but we can draw inspiration from it, sure. The sweater, the blazer, the trousers, it’s all there. I think I would maybe swap the pants for jeans and ditch the hat and gloves for my actual real life, but you do you! Also, I attempted to locate a bowler hat to add to this collage but failed; I suggest you shop vintage if your heart is set on it.
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When I rewatched the movie for this post, I actually noticed what we probably all thought was a black skirt on Sally is actually just long drapey shorts! Who knew?! I kept the skirt in the collage though for a similar look, but I’d buy these shorts if I were hoping to copy this look exactly. Add some tights, if you please.
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There’s that iconic sweater again, this time dressed up a bit more with jeans and sneakers.
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Omg, this scene! The way everyone is staring at her as she continues her ‘performance.’ Hysterical! No one is probably looking at her outfit, but I did. She’s wearing a white blouse buttoned to the top (ironic considering) under a thin gray v-neck cable knit. I’m not exactly sure what she’s wearing on bottom, but I took a guess with these navy trousers and black loafers. Fun fact - Danny and I visited this deli when we went to NYC a few years back on an anniversary trip.
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This right here is my favorite look of the whole movie - so much so I purchased this mockneck top to try and recreate this outfit for myself. I’ll definitely share on Instagram if it works out!
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This whole image is everything - the curly hair, the sleeves pushed up to the elbows, the glasses, the cluttered desk with the old school corded phone. Can this be my office? I do love the turtleneck here, but purple is not exactly my color; however, I can do burgundy - I’ve linked both options below.
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Read More:
Dressing Like Your Favorite RomCom Characters: Kathleen Kelly
Dressing Like Your Favorite RomCom Characters: Lucy Eleanor Moderatz
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