Style Inspo: When Harry Met Sally

This past weekend, I re-watched a small indie film you probably haven’t heard of called When Harry Met Sally (it was very niche, don’t feel bad) for what feels like the hundredth time. At the encouragement of a glass bottle of wine, I pulled a Kylie Jenner and started realising things.

For one, Carrie Fisher is in this movie. I have no idea how I never realised that before, but as Oprah says better late than never so now that I know she plays a main character in this cinematic masterpiece, I can appreciate it all the more.

The other thing I realised is that the fashion is so good. Like, really really good. The stuff of my dreams and numerous wishlists on my iPhone ‘Notes’ app.

And I’m not just talking about Sally. Harry has the best collection of mom (dad?) jeans I have ever seen. AND he pairs them all with chunky sweaters! I’m not drooling, you’re drooling.

So in honour of nothing in particular, I’ve decided to do a roundup of my fave looks from this movie. It was pretty hard to narrow them down because with the exception of that heinous bermuda shorts/knee high socks combo Meg Ryan must have been forced into against her will in the beginning of the movie (come on, no one aspires to dress like a park ranger. Including legitimate park rangers), everything was pretty much perfection.

Style Inspo: When Harry Met Sally []
let’s get this out of the way: the aforementioned bermuda tragedy of 1977.
Style Inspo: When Harry Met Sally []
These glasses were made to be worn with a turtleneck-blazer combo.
Style Inspo: When Harry Met Sally []
This is one of those instances where I can’t tell who wore it better. Points to Harry for the contrasting denim (dare I say… CANADIAN TUXEDO?), but also points to Sally for the cropped sweater/high waist jeans/blazer combo that is straight off my mood board. And yes, I have a mood board. Hop off.
Style Inspo: When Harry Met Sally []
To me the most memorable thing about the famous diner scene was the fact that Sally’s sandwich looks absolutely vile. There is a clear lack of condiment and the bread looks dry. But what she lacks in ordering decent food she more than makes up for with this embroidered button down tucked under a cable knit. Very librarian-chic, but in a good way.
Style Inspo: When Harry Met Sally []
THIS COAT. The shoulder pads. The cinched waist. The wide lapels. Never did I ever think I would get this excited about a brown article of clothing, but here we are.
Style Inspo: When Harry Met Sally []

Style Inspo: When Harry Met Sally []
Unfortunate bowler hat aside, this is an outfit I would willingly give up my pizza for. This blouse/high-waist pleated trousers combo is autumnal AF.
Style Inspo: When Harry Met Sally []
Do you know why Meg Ryan looks so blissfully content here? It’s because she knows she just pulled off the look of the century with the help of this pussy bow.
Style Inspo: When Harry Met Sally []
I picked this because I remember being thoroughly impressed that a movie character would dare to wear the same thing twice (see: same red turtleneck, pictured above). Not too shabby re: Harry’s dad jeans/sweater combo, either. I think I own that exact same outfit. Actually, I know I do.
Style Inspo: When Harry Met Sally []
And finally: my favourite look of the whole film. The high waist! The turtleneck! The big hair! The loafers! The socks in the loafers! It’s all too much. I need a moment.


  1. That movie is a classic! I totally didn’t realize Carrie Fisher was in it.


    Megan at Lush to Blush

  2. such a classic vday movie and such a totally fun post! love it!

  3. Great movie, and if you turned her glasses into shades, they would be killer!


  4. I love this movie so much! And I’m obsessed with this post!

    Greta |

  5. My all time favorite movie!! You’ve got me Lol’ing at their tragic style.

  6. I have yet to see this movie!! May need ot check it out.
    Amy | Pastel N Pink

  7. This is such a great movie! One of my favories. Their fashion is totally to die for!

  8. SO much love for this fashion! I always get so jealous of my mom, because when I look through old photos, she’s wearing stuff like this, and my kids are going to be stuck looking back on photos of me wearing leggings and Ugg boots.

    XO, SS || Seersucker Sass

  9. Michelle Paige

    I haven’t seen this movie but I looooove this type of fashion! Now I have to watch it!

    Michelle | She’s Not So Basic


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