When Harry Met Sally Outfits
Here’s how to recreate my favorite When Harry Met Sally outfits!
My rom com series is BACK with a classic: WHEN HARRY MET SALLY!!
In case you missed it, I started off with The Parent Trap which was a huge hit – and would also make great Halloween costumes! Then I moved on to a little You’ve Got Mail teaser (full video and post coming within the next few days!) along with My Best Friend’s Wedding reel and post.
But even when I was putting all of those together, I always knew that I needed to make one for When Harry Met Sally. I had a vision of this outfit in a bookstore from the very start, and quickly realized it also deserved it’s own roundup, too! It was made in 1989, so it’s not quite a 90’s rom com… but it’s close. And while some of the outfits I’ve put together feel a little costume-y for me to wear in everyday life, some of them are right on trend. If there’s one thing I love about TikTok, it’s that it made “Meg Ryan Fall” cool. Yes yes yes!
When Harry Met Sally Outfits
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Road Trip outfit
Okay when I mentioned a few of these are a little costume-y for me, this is really the one I’m talking about 😂 And the craziest part is that she wears long trouser SHORTS in the movie. I couldn’t go there, but I do think this look is pretty wearable… just with a little tweaking for me. I’d swap the shirt out for a tee and maybe grab a more feminine sweater. Then I’d be good to go! Shop the outfit here.
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Lunch Scene
If I had no issue, I would 1000% have gotten this jacket with this skirt or this tweed dress – but I actually love the way my look came together! This cardigan is usually hip length, but I tucked it under to make it shorter. So cute, right?! Shop the full outfit here.
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Bookstore Scene
As I mentioned, this is the first outfit that I thought of when I was brainstorming this series and it makes me SO HAPPY! I swapped the flat boots in the reel for heeled ones and it feels a little more feminine and fun this way. If this doesn’t scream Meg Ryan fall, I don’t know what does! Shop the full outfit here.
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Central Park Scene
This one is definitely the one I stretched the most since I would never wear that hat and I didn’t have a grey coat. But isn’t that the point of this series? Take an outfit and make it ME! Plus, I still think Meg would wear this while walking through Central Park, don’t you?! Shop the full outfit here.
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Apartment Scene
This outfit is so simple but SO GOOD. She’s actually wearing trouser shorts in the movie, but I couldn’t find any that fit me even remotely well so I opted for an a-line skirt I’ve had forever instead. That being said, this outfit is all about the red sweater and black tights anyway. Oh, and I gave her a Stanley cup because you know Sally would ditch plastic water bottles in 2022 😉 Shop the full outfit here.
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Karaoke Scene
Last but not least – this outfit reminds me of my Mom in the best way. I’m pretty sure I have a photo of her in something very similar circa 1989 😂 I couldn’t find an oversized mockneck like Meg’s so I sized up in this one s I could tuck it in and it’s honestly such a winner. Shop the full outfit here.
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shop more below including a black off the shoulder dress and green dress!
PS. You might also like Outfits Inspired By My Best Friend’s Wedding and Outfits Inspired By The Parent Trap!
