When Harry Met Sally (1989): Fashion in Film

One of my new favorite films, that I’d been desperately meaning to watch but forced to by my good friend Stella, is the iconic, fantastic, heartbreaking, and almost unfairly romantic is When Harry Met Sally. I absolutely love this movie, for oh-so many reasons that I won’t even go into (ranting Sof is not enjoyable Sof). But all you need to know is that it features young, naturally endearing Billy Crystal and Meg Ryan in New York City in 1989. If you have yet to watch this life-changing experience of a film, I suggest- no, I command you to go find it, whether it be iTunes, your parents’ old DVD collection (insane, right?), or even, perhaps, by finding it online somewhere (wink wink). I am not going to tell you any of the story, the plot, or really anything that will give the beauty of a classic away. Go. Now

As I watched it, I obsessively would keep my eyes on the gorgeous Meg Ryan’s style choices. I fell in love with both of the characters, (as any great film should make you do, usually) and I especially fell in love with the unique, 1989 standard outfits of Sally. I always say, if I could choose another time to live in, I would always choose the 80s. Perhaps all of the movies and television shows (Carrie Diaries, hello) I have watched have glorified the truth of the time period, but man, the style then seemed phenomenal. Ultra high waisted everything, so many collars, shoulder pads, and so much more. As a result of my love for Sally and even Harry’s unforgettable and on point outfits, I’ve decided to share a few of my favorite style moments from the film. Of course, there are some cringe-worthy choices, but we can totally and completely overlook them because pre-plastic surgery Meg Ryan (and Billy Crystal in leggings, need I say more?) could pull off anything. A talent indeed.


The poofy bob, the wispy bangs, the burgundy peter pan collar, the oversized blazer- need I say more? It all works, somehow, impossibly… it just does.




I really do love Sally’s outfit here, I must admit. The long brown coat, the adorable bright turtleneck, the high waisted jeans… Something about the whole outfit, which is typically seen as more masculine, makes her look all that much more feminine. 




Sally’s baby pink dress is simply adorable. It’s effortlessly feminine and chic, yet the scalloped neckline also adds sort of a playful nature to her look. Mixed with her messy, big blond hair, it looks gorgeous.



I think this is my favorite style moment from the movie. Sally looks cute as ever, with a classic, thick cropped turtleneck, a black skirt, tights, and boots- it all flows together so simply and almost artfully. Harry definitely steals the applause, though, because his iconic chunky white cableknit, paired with the bright blue skinny jeans and sneakers, is just, well… awesome.


Nobody else in this world, so far as I know, can pull off high waisted bermuda shorts, kneesocks, a button up, and a slightly large cardigan except for the one and only Meg Ryan. Kudos to you. 





This is one of the most iconic and well-known stills from the film. They both look wonderful, with Harry’s simple yet very city-like outfit, and Sally’s remarkably perfect getup. The hat, the high waisted harlem pants, the floral button down, the chic blazer, the bag…. it all just looks absolutely stunning. And with the lovely colors of fall behind them, the whole damn scene is perfect.

It’s a beautiful day to dream. 

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