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.
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.
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.
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.
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.
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.
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!